Sodium Hydroxide → 2-((2-chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylic Acid

HRID 1898331Notes

Reaction equation

HRID 1898331 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]3[CH2:17][C:18]([CH3:28])([CH3:27])[O:19][C:20]=3[C:21]([C:23]([O:25]C)=[O:24])=[CH:22][C:12]=2[N:11]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]3[CH2:17][C:18]([CH3:28])([CH3:27])[O:19][C:20]=3[C:21]([C:23]([OH:25])=[O:24])=[CH:22][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67503529methyl 2-((2-chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate

Product 1

HCID 675027202-((2-chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylic AcidYield 93.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared following the procedure described for Step-2 of Intermediate-3 using methyl 2-((2-chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (1.0 g, 2.47 mmol), Aq. NaOH (2.0 g, 50.0 mmol) and methanol (2.0 mL) to afford 0.9 g of desired product. 1HNMR (DMSO-d6): δ 1.46 (s, 6H), 3.34 (s, 2H), 3.53 (s, 3H), 6.99 (m, 1H), 7.06 (s, 1H), 7.18 (m, 1H), 7.27 (m, 1H), 10.36 (bs, 1H), 12.08 (bs, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-26d988f1df6d42fc84aa2ab9ac0c0d35
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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