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

HRID 1898433Notes

Reaction equation

HRID 1898433 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]([CH3:27])([CH3:26])[O:19][C:20]=3[C:21]([C:23](O)=[O:24])=[CH:22][C:12]=2[N:11]=1.S(Cl)(Cl)=O.[CH:32]1([C:35]2[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=2)[CH2:34][CH2:33]1.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[N:14]([CH3:15])[C:13]2[C:16]3[CH2:17][C:18]([CH3:26])([CH3:27])[O:19][C:20]=3[C:21]([C:23]([NH:39][C:38]3[CH:40]=[CH:41][C:35]([CH:32]4[CH2:34][CH2:33]4)=[CH:36][CH:37]=3)=[O:24])=[CH:22][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 122539274-CyclopropylanilineHCID 675027202-((2-chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylic Acid

Product 1

HCID 675033302-((2-Chloro-6-fluorophenyl)amino)-N-(4-cyclopropylphenyl)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamideYield 13.2%

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)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylic acid (Intermediate-49, 0.100 g, 0.256 mmol), thionyl chloride (2.0 mL), 4-cyclopropyl aniline (0.102 g, 0.769 mmol), THF (5.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.017 g of the desired product. 1HNMR (DMSO-d6): δ 0.62 (d, J=3.9 Hz, 2H), 0.91 (d, J=6.3 Hz, 2H), 1.60 (s, 6H), 1.88 (m, 1H), 3.45 (s, 2H), 3.55 (s, 3H), 6.98-7.16 (m, 3H), 7.19-7.36 (m, 3H), 7.53 (d, J=8.1 Hz, 2H), 9.60 (s, 1H), 10.48 (s, 1H); MS [M+H]+: 505.26.

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-39f297b0d4364535a002a72e2f5709ed
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…