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Diisopropylethylamine → 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid-[(R)-1-(3,4-diethyl-benzyl)-2-oxo-2-(4-piperazin-1-yl-piperidin-1-yl)-ethyl]-amide

HRID 644320
Notes
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Reaction equation

HRID 644320 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][C@@H:12]([NH:16][C:17]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[CH2:31][CH2:30][C:29]4[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=4[NH:27][C:26]3=[O:36])[CH2:21][CH2:20]2)=[O:18])[C:13](O)=[O:14])[CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.C([N:75]1[CH2:80][CH2:79][N:78]([CH:81]2[CH2:86][CH2:85][NH:84][CH2:83][CH2:82]2)[CH2:77][CH2:76]1)C1C=CC=CC=1>CCOC(C)=O.CN(C=O)C.C1COCC1>[CH2:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[CH2:11][C@@H:12]([NH:16][C:17]([N:19]1[CH2:20][CH2:21][CH:22]([N:25]2[CH2:31][CH2:30][C:29]3[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=3[NH:27][C:26]2=[O:36])[CH2:23][CH2:24]1)=[O:18])[C:13](=[O:14])[N:84]1[CH2:85][CH2:86][CH:81]([N:78]2[CH2:79][CH2:80][NH:75][CH2:76][CH2:77]2)[CH2:82][CH2:83]1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 36792751-Benzyl-4-piperidin-4-yl-piperazineHCID 68579001(R)-3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid

Product 1

HCID 59260968
4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid-[(R)-1-(3,4-diethyl-benzyl)-2-oxo-2-(4-piperazin-1-yl-piperidin-1-yl)-ethyl]-amide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 500 mg (1.02 mmol) (R)-3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid, 320 mg (1.09 mmol) TBTU, 0.22 mL (0.97 mmol) ethyldiisopropylamine and 45 mL THF was stirred for 1 h at RT, then combined with 310 mg (1.20 mmol) 1-benzyl-4-piperidin-4-yl-piperazine and 5 mL DMF and stirred overnight. The reaction mixture was diluted by the addition of 30 mL EtOAc, extracted with 30 mL of a 15% K2CO3 solution and the organic phase was dried. The organic phase was evaporated down under reduced pressure and the residue purified by chromatography on silica gel. The intermediate product fractions were evaporated down under reduced pressure, the residue remaining (260 mg) was dissolved in 20 mL MeOH and hydrogenated in the autoclave in the presence of 50 mg Pd/C (10%) at 50° C. and 3 bar hydrogen pressure until the calculated volume of hydrogen had been taken up. The catalyst was filtered off, the solvent eliminated under reduced pressure and the residue purified by chromatography on silica gel. The product fractions were evaporated down under reduced pressure, the residue was triturated with diisopropylether, suction filtered and dried.

Workup

  1. stirringstirred overnight
  2. extractionextracted with 30 mL of a 15% K2CO3 solution
  3. customthe organic phase was dried
  4. customThe organic phase was evaporated down under reduced pressure
  5. customthe residue purified by chromatography on silica gel
  6. customThe intermediate product fractions were evaporated down under reduced pressure
  7. dissolutionwas dissolved in 20 mL MeOH and hydrogenated in the autoclave in the presence of 50 mg Pd/C (10%) at 50° C.
  8. filtrationThe catalyst was filtered off
  9. customthe residue purified by chromatography on silica gel
  10. customThe product fractions were evaporated down under reduced pressure
  11. customthe residue was triturated with diisopropylether, suction
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-2fd646102c8b44f497e0d7077645feba
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700589B2

Reaction notes

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