HCID 59646493, compound → Methyl 2-((3,5-dichloropyridin-4-yl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate

HRID 1898354Notes

Reaction equation

HRID 1898354 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[C:12]=1[NH:13][CH3:14].[Cl:19][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([Cl:29])[C:25]=1[N:26]=[C:27]=S>C(#N)C>[Cl:19][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([Cl:29])[C:25]=1[NH:26][C:27]1[N:13]([CH3:14])[C:12]2[C:6]3[CH2:7][C:8]([CH3:11])([CH3:10])[O:9][C:5]=3[C:4]([C:15]([O:17][CH3:18])=[O:16])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 59646493HCID 59646493, compoundHCID 67503505Methyl 5-amino-2,2-dimethyl-4-(methylamino)-2,3-dihydrobenzofuran-7-carboxylate

Product 1

HCID 67502200Methyl 2-((3,5-dichloropyridin-4-yl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylateYield 59.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared following the procedure described for step-1 of Intermediate-3 using methyl 5-amino-2,2-dimethyl-4-(methylamino)-2,3-dihydrobenzofuran-7-carboxylate (step-6 of Intermediate-49, 2.00 g, 8.0 mmol), 3,5-dichloro-4-isothiocyanatopyridine (Intermediate-2, 1.96 g, 9.6 mmol), N,N-di-isopropyl carbodimide (0.5 mL) and acetonitrile (10.0 mL) to afford 2.0 g of the desired product. 1HNMR (DMSO-d6): 1.47 (s, 6H), 3.49 (s, 2H), 3.56 (s, 3H), 3.73 (s, 3H), 7.10 (s, 1H), 8.46 (s, 2H), 10.79 (s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-3996e3c193d84b758b6238f8e29f3778
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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