Thionyl Chloride → 2-((2-Chloro-6-fluorophenyl)amino)-N-(2-fluoro-4-methylphenyl)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide

HRID 1898396Notes

Reaction equation

HRID 1898396 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:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([OH:26])=O)=[CH:15][C:13]=2[N:14]=1.S(Cl)(Cl)=O.[F:31][C:32]1[CH:38]=[C:37]([CH3:39])[CH:36]=[CH:35][C:33]=1[NH2:34].CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:22])([CH3:23])[O:21][C:17]=3[C:16]([C:24]([NH:34][C:33]3[CH:35]=[CH:36][C:37]([CH3:39])=[CH:38][C:32]=3[F:31])=[O:26])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 679842-Fluoro-4-methylanilineHCID 81531DiisopropylethylamineHCID 178422815HCID 178422815, compound

Product 1

HCID 1784265502-((2-Chloro-6-fluorophenyl)amino)-N-(2-fluoro-4-methylphenyl)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamideYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure described for Example-108 using 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.150 g, 0.400 mmol), thionyl chloride (2.0 mL), 2-fluoro-4-methylaniline (0.075 g, 0.600 mmol), THF (5.0 mL) and DIPEA (3 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.100 g of the desired product. 1HNMR (DMSO-d6): δ 1.54 (s, 6H), 2.29 (s, 3H), 3.17 (s, 2H), 7.00 (d, J=8.4 Hz, 1H), 7.16 (d, J=12.3 Hz, 1H), 7.30 (s, 2H), 7.40 (m, 1H), 7.51 (s, 1H), 8.33 (t, J=8.4 Hz, 1H), 10.02 (s, 1H), 11.12 (s, 2H); MS [M+H]+: 483.17.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude product
  3. customwas purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH

Sources & evidence

ORD record
ord-115c5245d4e04f509f20ac819ec82fc2
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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