Thionyl Chloride → HCID 178481225, compound

HRID 1898421Notes

Reaction equation

HRID 1898421 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.[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][N+:34]=1[O-:43].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]([CH3:27])([CH3:26])[O:19][C:20]=3[C:21]([C:23]([NH:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]([F:40])([F:42])[F:41])=[CH:35][N+:34]=3[O-:43])=[O:24])=[CH:22][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 675027202-((2-chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylic AcidHCID 178507581HCID 178507581, compound

Product 1

HCID 178481225HCID 178481225, compoundYield 10.6%

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, 0.2564 mmol), thionyl chloride (2.0 mL), 2-amino-5-(trifluoromethyl)pyridine 1-oxide (Intermediate-41, 0.0835 g, 0.5128 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 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.60 (s, 6H), 3.49 (s, 2H), 3.53 (s, 3H), 7.02 (m, 1H), 7.18-7.36 (m, 3H), 7.80 (d, J=9.9 Hz, 1H), 8.64 (d, J=8.7 Hz, 1H), 8.95 (s, 1H), 10.56 (s, 1H), 12.21 (s, 1H); MS [M+H]+: 550.08.

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-1e44c12127ed4efe802477ce458a3773
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…