Dichloromethane → HCID 178502369, compound

HRID 1411367Notes

Reaction equation

HRID 1411367 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([C:35]5[N:36]=[C:37]([C@@H:40]6[CH2:44][CH2:43][CH2:42][N:41]6[C:45](=[O:55])[C@@H:46]([NH:50][C:51]([O:53][CH3:54])=[O:52])[CH:47]([CH3:49])[CH3:48])[NH:38][CH:39]=5)=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.ClCCl.FC(F)(F)C(O)=O>>[CH3:54][O:53][C:51](=[O:52])[NH:50][C@H:46]([C:45]([N:41]1[CH2:42][CH2:43][CH2:44][C@H:40]1[C:37]1[NH:38][CH:39]=[C:35]([C:32]2[CH:31]=[CH:30][C:29]([C:26]3[CH:27]=[CH:28][C:23]([C:21](=[O:22])[NH:20][C:17]4[CH:16]=[CH:15][C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[CH:19][CH:18]=4)=[CH:24][CH:25]=3)=[CH:34][CH:33]=2)[N:36]=1)=[O:55])[CH:47]([CH3:49])[CH3:48]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 178502370HCID 178502370, compound

Product 1

HCID 178502369HCID 178502369, compound

Procedure

To a solution of [4-{4-[(4′-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-biphenyl-4-carbonyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (42.4 mg, 0.0565 mmol) in dichloromethane (0.67 mL, 10 mmol) was added trifluoroacetic acid (0.3 mL, 0.004 mmol). The reaction mixture was stirred for 1 h at room temperature, concentrated, dissolved in methanol (1 mL), passed through a Stratospheres™ PL-CO3 resin, and the filtrate was concentrated to provide the title compound. (m/z): [M+H]+ calcd for C37H43N7O4 650.34 found 650.8.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in methanol (1 mL)
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-17344b0d5b184687a2d0e9032eec14ac
Source dataset
uspto-grants-2014_12
Patent number
US08921372B2

Reaction notes

Loading…