HCID 67503724, compound → HCID 178496984, compound

HRID 1898325Notes

Reaction equation

HRID 1898325 reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=1[NH2:17].[Cl:18][C:19]1[C:24]([N:25]=[C:26]=S)=[C:23]([CH3:28])[CH:22]=[CH:21][N:20]=1>C(#N)C>[Cl:18][C:19]1[C:24]([NH:25][C:26]2[NH:1][C:2]3[C:7]4[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=4[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=3[N:17]=2)=[C:23]([CH3:28])[CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 67503724HCID 67503724, compoundHCID 866646912-Chloro-3-isothiocyanato-4-methylpyridine

Product 1

HCID 178496984HCID 178496984, compoundYield 229.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared following the procedure described for Step-1 of Intermediate-3 using methyl 4,5-diamino-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate (Intermediate-1, 1.00 g, 0.450 mmol), acetonitrile (10.0 mL), 2-chloro-3-isothiocyanato-4-methylpyridine (Step 1 product, 0.95 g, 0.521 mmol) and N,N-di-isopropyl carbodimide (2.0 mL) to afford 0.400 g of the desired product. 1HNMR (DMSO-d6): δ 1.42 (s, 6H), 2.24 (s, 3H), 2.98 (s, 2H), 3.72 (s, 3H), 7.31 (s, 1H), 7.37 (d, J=4.8 Hz, 1H), 8.15 (d, 1H), 10-11 (s, 2H); MS [M+H]+: 387.24.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-8b613841024d454ca674554d4a5e4b35
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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