Trifluoroacetic acid → 13-cyclohexyl-6-(1-cyclopropyl-4-(ethoxycarbonyl)-3-isopropyl-1H-pyrazol-5-yl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxylic Acid

HRID 1094541Notes

Reaction equation

HRID 1094541 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]1([C:14]2[C:15]3[CH:16]=[CH:17][C:18]([C:50]([O:52]C(C)(C)C)=[O:51])=[CH:19][C:20]=3[N:21]3[CH2:27][C:26]([C:28]4[N:32]([CH:33]5[CH2:35][CH2:34]5)[N:31]=[C:30]([CH:36]([CH3:38])[CH3:37])[C:29]=4[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:25][C:24]4[CH:44]=[C:45]([O:48][CH3:49])[CH:46]=[CH:47][C:23]=4[C:22]=23)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>ClC(Cl)C>[CH:8]1([C:14]2[C:15]3[CH:16]=[CH:17][C:18]([C:50]([OH:52])=[O:51])=[CH:19][C:20]=3[N:21]3[CH2:27][C:26]([C:28]4[N:32]([CH:33]5[CH2:34][CH2:35]5)[N:31]=[C:30]([CH:36]([CH3:37])[CH3:38])[C:29]=4[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:25][C:24]4[CH:44]=[C:45]([O:48][CH3:49])[CH:46]=[CH:47][C:23]=4[C:22]=23)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57953852tert-butyl 13-cyclohexyl-6-(1-cyclopropyl-4-(ethoxycarbonyl)-3-isopropyl-1H-pyrazol-5-yl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxylate

Product 1

HCID 5795385013-cyclohexyl-6-(1-cyclopropyl-4-(ethoxycarbonyl)-3-isopropyl-1H-pyrazol-5-yl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxylic AcidYield 99.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

TFA (2.8 mL, 37 mmol) was added to a stirring solution of tert-butyl 13-cyclohexyl-6-(1-cyclopropyl-4-(ethoxycarbonyl)-3-isopropyl-1H-pyrazol-5-yl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxylate (350 mg, 0.527 mmol) in dichloroethane (5 mL) at room temperature. The reaction was allowed to stir for 2.5 hrs and then was concentrated to dryness to give expected product (320 mg, 0.526 mmol, quant) consistent by LCMS.

Workup

  1. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-3b1c9a8aeaf84107a7587788f42db22d
Source dataset
uspto-grants-2012_03
Patent number
US08133884B2

Reaction notes

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