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-(4-dimethylamino-piperidin-1-yl)-2-oxo-ethyl]-amide

HRID 644316Notes

Reaction equation

HRID 644316 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.[CH3:68][N:69]([CH3:76])[CH:70]1[CH2:75][CH2:74][NH:73][CH2:72][CH2:71]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]([N:73]1[CH2:74][CH2:75][CH:70]([N:69]([CH3:76])[CH3:68])[CH2:71][CH2:72]1)=[O:14])[CH3:2]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 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 592609884-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid-[(R)-1-(3,4-diethyl-benzyl)-2-(4-dimethylamino-piperidin-1-yl)-2-oxo-ethyl]-amide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 400 mg (0.81 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, 280 mg (0.87 mmol) TBTU, 0.17 mL (0.97 mmol) ethyldiisopropylamine and 45 mL THF was stirred for 1 h at RT, then combined with 130 mg (1.01 mmol) dimethyl-piperidin-4-yl-amine 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 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 product fractions were evaporated down under reduced pressure
  5. customthe residue was triturated with diisopropylether, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-ad568ad34ed34ceab4750d1e74f41a8e
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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