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

HRID 1678516Notes

Reaction equation

HRID 1678516 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[C:14](=[O:32])[NH:15][C:16]1[CH:17]=[C:18]([C:23]2[CH:28]=[CH:27][C:26]([C:29](O)=[O:30])=[CH:25][CH:24]=2)[C:19]([Cl:22])=[CH:20][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:33]([S:36]([N:39]1[CH2:44][CH2:43][N:42]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([NH2:52])=[CH:48][CH:47]=2)[CH2:41][CH2:40]1)(=[O:38])=[O:37])[CH2:34][CH3:35].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[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[C:14](=[O:32])[NH:15][C:16]1[CH:17]=[C:18]([C:23]2[CH:24]=[CH:25][C:26]([C:29](=[O:30])[NH:52][C:49]3[CH:50]=[CH:51][C:46]([CH2:45][N:42]4[CH2:41][CH2:40][N:39]([S:36]([CH2:33][CH2:34][CH3:35])(=[O:38])=[O:37])[CH2:44][CH2:43]4)=[CH:47][CH:48]=3)=[CH:27][CH:28]=2)[C:19]([Cl:22])=[CH:20][CH:21]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 282735484-[(4-(Propylsulfonyl)piperazin-1-yl)methyl]anilineHCID 67373093(R)-2-(4'-Carboxy-6-chloro-biphenyl-3-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67373676(R)-2-{6-Chloro-4'-[4-(4-(propane-1-sulfonyl)-piperazin-1-ylmethyl)-phenylcarbamoyl]-biphenyl-3-ylcarbamoyl}-piperidine-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)-piperidine-1-carboxylic acid tert-butyl ester (73 mg), 4-(4-(propane-1-sulfonyl)-piperazin-1-ylmethyl)-phenylamine (118 mg) and HBTU (91 mg) in dry DMF (4 ml) containing N-methylmorpholine (52 μl) was stirred at room temp for 18 h.

Sources & evidence

ORD record
ord-48e1734bab90407986c8be473952b39a
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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