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

HRID 1486416Notes

Reaction equation

HRID 1486416 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:31][N:10]2[C:11]3[CH:12]=[C:13]([C:24]([O:26]C(C)(C)C)=[O:25])[CH:14]=[CH:15][C:16]=3[C:17]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]2[C:8]2[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[CH:35][C:7]=2[CH:6]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH2:31][N:10]2[C:11]3[CH:12]=[C:13]([C:24]([OH:26])=[O:25])[CH:14]=[CH:15][C:16]=3[C:17]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]2[C:8]2[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[CH:35][C:7]=2[CH:6]=1)=[O:4]

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 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13-Cyclohexyl-3-methoxy-7H-benzo[3,4]azepino[1,2-a]indole-6,10-dicarboxylic acid 10-tert-butyl ester 6-methyl ester 1a (1 g, 1 eq) was dissolved in dry dichloromethane under N2, followed by the addition of trifluoroacetic acid (TFA) (8.88 ml, 60 eq). The solution was stirred at RT for 24 h. The solvent was then removed under reduced pressure. The crude product was triturated with diethyl ether. The crystals were filtered off and dried under vacuum overnight to afford the title product 13-Cyclohexyl-3-methoxy-7H-benzo[3,4]azepino[1,2-a]indole-6,10-dicarboxylic acid 6-methyl ester 13a (89%, 0.86 g); LC-MS: Rt. 3.19 min., m/z 446 [M+H]+.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customThe crude product was triturated with diethyl ether
  3. filtrationThe crystals were filtered off
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-3a0e77ffc4fb426cbf671602b9e934aa
Source dataset
uspto-grants-2016_08
Patent number
US09427440B2

Reaction notes

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