4-Methylmorpholine → (R)-2-{6-Chloro-4'-[4-(4-methanesulfonyl-piperazin-1-ylmethyl)-phenylcarbamoyl]-biphenyl-3-ylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1678513Notes

Reaction equation

HRID 1678513 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13](=[O:31])[NH:14][C:15]1[CH:16]=[C:17]([C:22]2[CH:27]=[CH:26][C:25]([C:28](O)=[O:29])=[CH:24][CH:23]=2)[C:18]([Cl:21])=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:32][S:33]([N:36]1[CH2:41][CH2:40][N:39]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][CH:44]=2)[CH2:38][CH2:37]1)(=[O:35])=[O:34].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13](=[O:31])[NH:14][C:15]1[CH:16]=[C:17]([C:22]2[CH:23]=[CH:24][C:25]([C:28](=[O:29])[NH:49][C:46]3[CH:47]=[CH:48][C:43]([CH2:42][N:39]4[CH2:38][CH2:37][N:36]([S:33]([CH3:32])(=[O:35])=[O:34])[CH2:41][CH2:40]4)=[CH:44][CH:45]=3)=[CH:26][CH:27]=2)[C:18]([Cl:21])=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 113692314-(4-Methanesulfonyl-piperazin-1-ylmethyl)-phenylamineHCID 67372818(R)-2-(4'-Carboxy-6-chloro-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67370744(R)-2-{6-Chloro-4'-[4-(4-methanesulfonyl-piperazin-1-ylmethyl)-phenylcarbamoyl]-biphenyl-3-ylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (R)-2-(4′-Carboxy-6-chloro-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (100 mg), 4-(4-methanesulfonyl-piperazin-1-ylmethyl)-phenylamine (86 mg) and HBTU (121 mg) in dry DMF (4 ml) containing N-methylmorpholine (69 μl) was stirred at room temp for 18 h.

Sources & evidence

ORD record
ord-1cc5ad6e155e4f11bc38ae533b2f275e
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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