Trifluoroacetic acid → 7-Methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carboxylic acid benzo[b]thiophen-2-ylmethyl-[(2S,3aS,7aS)-1-(octahydro-indol-2-yl)methyl]-amide

HRID 2220715Notes

Reaction equation

HRID 2220715 reaction equation
C(OC([N:8]1[C@@H:16]2[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][C@H:9]1[CH2:17][NH:18][CH2:19][C:20]1[S:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[CH:21]=1)=O)(C)(C)C.C(N(CC)CC)C.[CH3:36][O:37][C:38]1[C:43]2[O:44][C:45]([CH3:48])([CH3:47])[O:46][C:42]=2[CH:41]=[C:40]([C:49](Cl)=[O:50])[CH:39]=1.FC(F)(F)C(O)=O>ClCCl>[S:24]1[C:20]([CH2:19][N:18]([CH2:17][C@@H:9]2[CH2:10][C@H:11]3[C@H:16]([CH2:15][CH2:14][CH2:13][CH2:12]3)[NH:8]2)[C:49]([C:40]2[CH:39]=[C:38]([O:37][CH3:36])[C:43]3[O:44][C:45]([CH3:48])([CH3:47])[O:46][C:42]=3[CH:41]=2)=[O:50])=[CH:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]1=2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 58622260(2S,3aS,7aS)-2-{[(Benzo[b]thiophen-2-ylmethyl)-amino]-methyl}-octahydro-indole-1-carboxylic acid tert-butyl esterHCID 714100777-Methoxy-2,2-dimethyl-2H-1,3-benzodioxole-5-carbonyl chloride

Product 1

HCID 586221297-Methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carboxylic acid benzo[b]thiophen-2-ylmethyl-[(2S,3aS,7aS)-1-(octahydro-indol-2-yl)methyl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Experimental conditions analogous to Example 1, from 0.12 (0.31 mmol) of (2S,3aS,7aS)-2-{[(benzo[b]thiophen-2-ylmethyl)-amino]-methyl}-octahydro-indole-1-carboxylic acid tert-butyl ester, 3 mL dichloromethane, 52 μL (0.37 mmol) of triethylamine, and 83 mg (0.34 mmol) of 7-methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carbonyl chloride and 0.4 mL trifluoroacetic acid. The compound was purified using reverse phase HPLC, mobile phase with a gradient 15-80% acetonitrile in 50 min, gave 104 mg of the product as the free base as an off-white solid. LC-MSD, m/z for C29H34N2O4S [M+H]+: 507.6. 1H NMR (400 MHz, CDCl3/HCl): δ 1.4-2.0 (m, 8 H), 1.7 (s, 6 H), 2.1-2.2 (m, 1 H), 2.4-2.5 (m, 1 H), 3.2 (bs, 1 H), 3.3-3.4 (m, 1 H), 3.7-3.8 (m, 1 H), 3.8 (s, 3 H), 4.2-4.4 (m, 2 H), 4.9-5.2 (m, 2 H), 6.8 (s, 1 H), 7.1 (s, 1 H), 7.3-7.4 (m, 2 H), 7.7-7.8 (m, 2 H), 7.9 (bs, 1 H), 11.6-11.8 (bs, 1 H).

Workup

  1. customThe compound was purified
  2. customin 50 min

Sources & evidence

ORD record
ord-79a2a7754aac4e50afd345ca9aa67178
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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