Hydrochloric Acid → 3-Cyano-4-(2-methylphenyl)-1-(3-(1-naphthyloxy)propyl)-1h-indole-2-carboxylic acid

HRID 1013309Notes

Reaction equation

HRID 1013309 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[N:5]([CH2:19][CH2:20][CH2:21][O:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[C:4]=1[C:33]([O:35]C)=[O:34])#[N:2].[OH-].[Na+].Cl>O1CCCC1.CO>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[N:5]([CH2:19][CH2:20][CH2:21][O:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[C:4]=1[C:33]([OH:35])=[O:34])#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67315489Methyl 3-cyano-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1h-indole-2-carboxylate

Product 1

HCID 673154113-Cyano-4-(2-methylphenyl)-1-(3-(1-naphthyloxy)propyl)-1h-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of EXAMPLE 133A (16 mg) and sodium hydroxide (200 μl) in tetrahydrofuran (0.5 ml) and methanol (0.5 ml) was stirred overnight, neutralized with diluted HCl, and concentrated. The residue was purified by RPHPLC to provide the desired product. 1H NMR (500 MHz, dimethyl sulfoxide-d6) δ 14.24 (s, 1H), 8.14 (d, J=8.54 Hz, 1H), 7.86 (dd, J=7.48, 5.65 Hz, 2H), 7.35-7.61 (m, 5H), 7.18-7.36 (m, 3H), 7.12 (d, J=7.32 Hz, 1H), 7.06 (d, J=7.02 Hz, 1H), 6.89 (d, J=7.32 Hz, 1H), 4.77-5.18 (m, 2H), 4.24 (t, J=5.03 Hz, 2H), 2.30-2.47 (m, 2H), 1.99 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by RPHPLC

Sources & evidence

ORD record
ord-d0295556b8ac46bcb39b987525f61475
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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