Diisopropylethylamine → HCID 23653774, compound

HRID 644351Notes

Reaction equation

HRID 644351 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:30]([OH:32])=O)[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[C:22]([CH2:28][CH3:29])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:33]=[CH:34][CH:35]=[CH:36][C:4]=2[NH:3]1.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]1[CH2:74][CH2:73][CH:72]([N:75]2[CH2:80][CH2:79][NH:78][CH2:77][CH2:76]2)[CH2:71][CH2:70]1.C([O-])(O)=O.[Na+]>CN(C=O)C.C1COCC1>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[C:22]([CH2:28][CH3:29])[CH:21]=3)[C:30]([N:78]3[CH2:77][CH2:76][N:75]([CH:72]4[CH2:73][CH2:74][N:69]([CH3:68])[CH2:70][CH2:71]4)[CH2:80][CH2:79]3)=[O:32])=[O:16])[CH2:13][CH2:14]2)[CH2:7][CH2:6][C:5]2[CH:33]=[CH:34][CH:35]=[CH:36][C:4]=2[NH:3]1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68578903HCID 68578903, compound

Product 1

HCID 23653774HCID 23653774, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 150 mg (0.30 mmol) (R)-1-carboxy-2-(3,4-diethyl-phenyl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 98 mg (0.30 mmol) TBTU, 0.2 mL (1.1 mmol) ethyldiisopropylamine and 15 mL THF as well as 3 mL DMF was stirred for 1 h at RT, then combined with 56 mg (0.30 mmol) 1-(1-methyl-piperidin-4-yl)-piperazin and stirred for 2 h. The reaction mixture was combined with 30 mL of a semisaturated NaHCO3 solution and extracted with 30 mL EtOAc. The organic phase was dried, evaporated down under reduced pressure and the residue was 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 for 2 h
  2. extractionextracted with 30 mL EtOAc
  3. customThe organic phase was dried
  4. customevaporated down under reduced pressure
  5. customthe residue was purified by chromatography on silica gel
  6. customThe product fractions were evaporated down under reduced pressure
  7. customthe residue was triturated with diisopropylether, suction
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-b3863ef797ea411eb0c67a6ea90cc143
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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