Trifluoroacetic acid → 13-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 1723944Notes

Reaction equation

HRID 1723944 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([C:14]2[C:15]3[CH:16]=[CH:17][C:18]([C:38]([O:40]C(C)(C)C)=[O:39])=[CH:19][C:20]=3[N:21]3[CH2:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][C:24]4[CH:32]=[C:33]([O:36][CH3:37])[CH:34]=[CH:35][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:38]([OH:40])=[O:39])=[CH:19][C:20]=3[N:21]3[CH2:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][C:24]4[CH:32]=[C:33]([O:36][CH3:37])[CH:34]=[CH:35][C:23]=4[C:22]=23)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 5983755810-tert-butyl 6-methyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate

Product 1

HCID 5755909813-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Trifluoroacetic acid (30 mL) was added dropwise to a stirring slurry of 10-tert-butyl 6-methyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate (10 g, 20 mmol) in dichloroethane (30 mL) under N2. The clear dark green solution was stirred at rt for 2.5 h, concentrated to dryness and stirred with EtOAc (100 mL) overnight. The solids were collected by filtration, washed with EtOAc and Et2O to yield 13-cyclohexyl-3-methoxy-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid (8.35 g, 18.8 mmol, 94%) was as a yellow solid which was used without further purification. 1HNMR (300 MHz, CDCl3) δ 1.13-2.16 (m, 10H), 2.74-2.88 (m, 1H), 3.84 (s, 3H), 3.89 (s, 3H), 4.06-4.29 (m, 1H), 5.54-5.76 (m, 1H), 6.98 (d, J=2.6 Hz, 1H), 7.08 (dd, J=8.4, 2.6 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.78 (dd, J=8.8, 1.1 Hz, 1H), 7.80 (s, 1H), 7.86 (d, J=8.8 Hz, 1H), 8.34 (d, J=1.1 Hz, 1H). LCMS: m/e 446 (M+H)+, ret time 3.21 min, column B, 4 minute gradient.

Workup

  1. concentrationconcentrated to dryness
  2. stirringstirred with EtOAc (100 mL) overnight
  3. filtrationThe solids were collected by filtration
  4. washwashed with EtOAc and Et2O

Sources & evidence

ORD record
ord-454dcc6857b84fb285f233f6f756114e
Source dataset
uspto-grants-2009_02
Patent number
US07485633B2

Reaction notes

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