Acetic Acid → HCID 178496996, compound

HRID 1898347Notes

Reaction equation

HRID 1898347 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[NH:14][C:13]2[C:15]([N+:24]([O-])=O)=[C:16]([OH:23])[C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:12]=2[N:11]=1.[In].[C:28](O)(=O)[CH3:29].C(OC)(OC)(OC)C>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:14][C:13]2[C:15]3[N:24]=[C:28]([CH3:29])[O:23][C:16]=3[C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 15050Trimethyl orthoacetateHCID 5359967IndiumHCID 178496999HCID 178496999, compound

Product 1

HCID 178496996HCID 178496996, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The title compound was prepared following the procedure described for step-4 of Intermediate-55 using methyl 2-[(2-chloro-6-fluorophenyl)amino]-6-hydroxy-7-nitro-1H-benzimidazole-5-carboxylate (0.320 g, 0.840 mmol), benzene (6 mL), indium (0.386 g, 3.363 mmol), acetic acid (0.505 g, 8.40 mmol) and trimethyl orthoacetate (0.812 g, 2.96 mmol) to afford 0.195 g of the desired product. 1HNMR (DMSO-d6): δ 2.63 (s, 3H), 3.88 (s, 3H), 7.439-7.46 (m, 3H), 7.71 (s, 1H), 9.0-10.0 (s, 1H), 11.60 (s, 1H); MS [M+H]+: 375.34.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-0d9f9ab7962a483ba9cc036e9fe0a534
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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