Thionyl Chloride → 2-((3,5-Dichloropyridin-4-yl)amino)-1,7,7-trimethyl-N-(5-(trifluoromethyl)pyridin-2-yl)-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide

HRID 1898484Notes

Reaction equation

HRID 1898484 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[NH:8][C:9]1[N:13]([CH3:14])[C:12]2[C:15]3[CH2:16][C:17]([CH3:26])([CH3:25])[O:18][C:19]=3[C:20]([C:22](O)=[O:23])=[CH:21][C:11]=2[N:10]=1.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N+:30]=1[O-].S(Cl)(Cl)=O.CCN(C(C)C)C(C)C>[Fe].C(O)(=O)C.C1COCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[NH:8][C:9]1[N:13]([CH3:14])[C:12]2[C:15]3[CH2:16][C:17]([CH3:26])([CH3:25])[O:18][C:19]=3[C:20]([C:22]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:37])([F:36])[F:38])=[CH:31][N:30]=3)=[O:23])=[CH:21][C:11]=2[N:10]=1

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 67502982HCID 67502982, compoundHCID 178507581HCID 178507581, compound

Product 1

HCID 675027982-((3,5-Dichloropyridin-4-yl)amino)-1,7,7-trimethyl-N-(5-(trifluoromethyl)pyridin-2-yl)-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamideYield 9.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the same procedure described for Example-205 by using 2-((3,5-dichloropyridin-4-yl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylic acid (Intermediate-61, 0.200 g, 0.491 mmol), 2-Amino-5-(trifluoromethyl)pyridine 1-oxide (Intermediate-41, 0.131 g, 0.737 mmol), thionyl chloride (2 mL), DIPEA (10 mL), THF (5.0 mL), acetic acid (10.0 mL), iron powder (0.200 g) to afford 0.025 g of the desired product. 1HNMR (DMSO-d6): δ 1.61 (s, 6H), 3.52 (s, 2H), 3.60 (s, 3H), 7.31 (s, 1H), 8.23 (d, J=10.5 Hz, 1H), 8.44 (s, 1H), 8.48 (s, 2H), 8.76 (s, 1H), 10.40 (s, 1H), 10.93 (s, 1H); MS [M]+: 551.07.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-5b9f4ff1f65846bc9a7c561d7d471022
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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