4-Methylmorpholine → HCID 86588694, compound

HRID 636985Notes

Reaction equation

HRID 636985 reaction equation
[C:1]([NH:4][C@H:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])(=[O:3])[CH3:2].[NH2:29][CH2:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[C:37]([NH2:41])=[N:36][CH:35]=[CH:34]2.CN1CCOCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[NH2:41][C:37]1[C:38]2[C:33](=[CH:32][C:31]([CH2:30][NH:29][C:13]([C@@H:9]3[CH2:10][CH2:11][CH2:12][N:8]3[C:6](=[O:7])[C@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:21][CH:22]=3)=[O:15])=[CH:40][CH:39]=2)[CH:34]=[CH:35][N:36]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 221697756-(Aminomethyl)isoquinolin-1-amineHCID 229584291-(2-(R)-Acetylamino-3-biphenyl-4yl-propionyl)-pyrrolidine-2-(S)-carboxylic acid

Product 1

HCID 86588694HCID 86588694, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-(R)-acetylamino-3-biphenyl-4y1-propionyl)-pyrrolidin-2-(S)-carboxylic acid (0.120 g), 6-aminomethyl-isoquinolin-1-ylamine (0.058 g), N-methyl morpholine (0.11 mL) and 0.100 g of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) in 4.5 mL of dry N,N-dimethyl formamide was stirred for 3 h at ambient temperature. The mixture was concentrated and the remaining residue was purified by silica chromatography (dichloro-methane/methanol 8/2) to give 0.120 g (70%) of the title compound as a light yellow solid. (+)- APCI-MS: 536 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe remaining residue was purified by silica chromatography (dichloro-methane/methanol 8/2)

Sources & evidence

ORD record
ord-4b4b394eedfc4be596f48ff3c2edb6a0
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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