Hydrochloric Acid → HCID 53260305, compound

HRID 2370341Notes

Reaction equation

HRID 2370341 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:12](=[O:49])[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([C:30]3[C:38]4[C:33](=[C:34]([F:44])[CH:35]=[CH:36][C:37]=4[O:39][C:40]([F:43])([F:42])[F:41])[N:32]([CH2:45][CH2:46][O:47][CH3:48])[CH:31]=3)=[O:29])[CH2:24][CH2:23]2)[CH:16]=1)[CH:9]([CH3:11])[CH3:10])(C)(C)C.[ClH:51]>CCOCC>[ClH:51].[NH2:7][C@@H:8]([CH:9]([CH3:11])[CH3:10])[C:12]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([C:30]3[C:38]4[C:33](=[C:34]([F:44])[CH:35]=[CH:36][C:37]=4[O:39][C:40]([F:41])([F:42])[F:43])[N:32]([CH2:45][CH2:46][O:47][CH3:48])[CH:31]=3)=[O:29])[CH2:24][CH2:23]2)[CH:16]=1)=[O:49]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68228638HCID 68228638, compound

Product 1

HCID 53260305HCID 53260305, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of [(S)-1-(4-fluoro-3-{1-[7-fluoro-1-(2-methoxy-ethyl)-4-trifluoromethoxy-1H-indole-3-carbonyl]-piperidin-4-yl}-benzylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester (0.35 g, 0.49 mmol) in ether (20 mL) was added 2M HCl in ether (10 mL, 20.0 mmol). The reaction mixture was stirred at rt overnight. The resulting precipitate was collected to give the titled compound (260 mg, 82%). 1H NMR (300 MHz, DMSO-d6) δ 9.0 (m, 1H), 8.3 (bs, 2H), 7.7 (s, 1H), 7.3-7.0 (m, 5H), 4.5 (m, 2H), 4.4-4.2 (m, 2H), 3.7-3.5 (m, 6H), 3.2 (s, 3H), 3.1-2.9 (m, 2H), 2.1 (m, 1H), 1.85-1.5 (m, 4H), 0.9 (m, 6H). MS m/z: [M+H]+=611.

Workup

  1. customThe resulting precipitate was collected

Sources & evidence

ORD record
ord-1787fa5e990647f2ac475e81de4b04eb
Source dataset
uspto-grants-2014_04
Patent number
US08710080B2

Reaction notes

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