4-Methylmorpholine → {2-[3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-pyridin-2-yl-amino)-propionylamino]-ethyl}-carbamic acid tert-butyl ester

HRID 449746Notes

Reaction equation

HRID 449746 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21]([N:23]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH2:24][CH2:25][C:26](O)=[O:27])=[O:22])=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.[C:64]([O:68][C:69](=[O:74])[NH:70][CH2:71][CH2:72][NH2:73])([CH3:67])([CH3:66])[CH3:65]>O1CCCC1.O.C(OCC)(=O)C>[C:64]([O:68][C:69](=[O:74])[NH:70][CH2:71][CH2:72][NH:73][C:26](=[O:27])[CH2:25][CH2:24][N:23]([C:21]([C:19]1[CH:18]=[CH:17][C:14]2[N:15]([CH3:16])[C:11]([CH2:10][NH:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[N:12][C:13]=2[CH:20]=1)=[O:22])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)([CH3:67])([CH3:65])[CH3:66]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 187201N-BOC-ethylenediamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18412686N-[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-beta-alanine

Product 1

HCID 66706334{2-[3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-pyridin-2-yl-amino)-propionylamino]-ethyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of 2a (2.20 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 2.20 mmol) and N-methyl-morpholin (2.20 mmol) in dry tetrahydrofuran (100 mL) was stirred at room temperature for 15 minutes. Then (2-amino-ethyl)-carbamic acid tert-butyl ester (2.20 mmol) was added and the mixture stirred at room temperature for another 24 hours. The mixture was then diluted with 40 mL water, the product was isolated through extraction with ethyl acetate and purified by chromatography (silica gel; dichloromethane/methanol 15:1).

Workup

  1. custompurified by chromatography (silica gel; dichloromethane/methanol 15:1)

Sources & evidence

ORD record
ord-2833521b91bb4b8da594ad96c267fc53
Source dataset
uspto-grants-2013_07
Patent number
US08486398B2

Reaction notes

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