Ammonia → HCID 69418321, compound

HRID 1373202Notes

Reaction equation

HRID 1373202 reaction equation
C[O:2][C:3]([C:5]1([F:25])[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:17]=2[F:24])=[CH:13][C:8]2=[N:9][CH2:10][N:11]([CH3:12])[C:7]2=[CH:6]1)=O.[NH3:26]>>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:14]2[C:5]([F:25])([C:3]([NH2:26])=[O:2])[CH:6]=[C:7]3[N:11]([CH3:12])[CH2:10][N:9]=[C:8]3[CH:13]=2)=[C:17]([F:24])[CH:18]=1)[CH3:23]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 69420062HCID 69420062, compound

Product 1

HCID 69418321HCID 69418321, compoundYield 65%

Procedure

A solution of 6-(4-Ethyl-2-fluoro-phenylamino)-5-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester (0.309 g) in ammonia-saturated isopropanol (10 mL) was heated in a sealed pressure tube at 80° C. for 80 h. The resultant reaction mixture was concentrated to dryness and recrystallized from ethanol to afford pure 6-(4-ethyl-2-fluoro-phenylamino)-5-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid amide (0.199 g, 65% yield): m.p. 249–251° C.; 1H NMR (400 MHz, acetone-d6) δ 8.45 (brs, 1 H), 8.18 (s, 1 H), 5.94 (s, 1 H), 5.59 (br s, 1 H), 6.95 (dd, J=12.5, 2.0 Hz, 1 H), 6.89 (br s, 1 H), 6.81 (br d, 1 H), 6.56 (td, J=8.6, 4.9 Hz, 1 H), 3.95 (s, 3 H), 2.54 (q, J=5.6 Hz, 2 H), 1.16 (t, J=5.6 Hz, 3 H). Anal. Calcd/Found for C15H16F2N4O: C, 61.64/61.26; H, 4.88/4.84; N, 16.96, 16.68; F, 11.50/11.85.

Workup

  1. customThe resultant reaction mixture
  2. concentrationwas concentrated to dryness
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1427d0cf6db748a5bb253fbae93e29f4
Source dataset
uspto-grants-2007_01
Patent number
US07160915B2

Reaction notes

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