4-Cyclopropylaniline → N-(4-Cyclopropylphenyl)-2-((3,5-dichloropyridin-4-yl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide

HRID 1898481Notes

Reaction equation

HRID 1898481 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:28])[C:7]=1[NH:8][C:9]1[N:13]([CH3:14])[C:12]2[C:15]3[CH2:16][C:17]([CH3:27])([CH3:26])[O:18][C:19]=3[C:20]([C:22]([O:24]C)=O)=[CH:21][C:11]=2[N:10]=1.[CH:29]1([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)[CH2:31][CH2:30]1.C[Al](C)C>C1(C)C=CC=CC=1>[CH:29]1([C:32]2[CH:38]=[CH:37][C:35]([NH:36][C:22]([C:20]3[C:19]4[O:18][C:17]([CH3:26])([CH3:27])[CH2:16][C:15]=4[C:12]4[N:13]([CH3:14])[C:9]([NH:8][C:7]5[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=5[Cl:28])=[N:10][C:11]=4[CH:21]=3)=[O:24])=[CH:34][CH:33]=2)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 122539274-CyclopropylanilineHCID 16682925TrimethylaluminumHCID 67502200Methyl 2-((3,5-dichloropyridin-4-yl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate

Product 1

HCID 56968488N-(4-Cyclopropylphenyl)-2-((3,5-dichloropyridin-4-yl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamideYield 35.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure described for Example-143 by using methyl 2-((3,5-dichloropyridin-4-yl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (Intermediate-60, 0.100 g, 0.245 mmol), 4-cyclopropylaniline (Intermediate-50, 0.047 g, 0.356 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL), dry toluene (5.0 mL) to afford 0.045 g of the desired product. 1HNMR (DMSO-d6): δ 0.63 (m, 2H), 0.91 (d, J=6.6 Hz, 2H), 1.60 (s, 6H), 1.89 (m, 1H), 3.48 (s, 2H), 3.59 (s, 3H), 7.05 (d, J=7.8 Hz, 2H), 7.26 (s, 1H), 7.54 (d, J=8.1 Hz, 2H), 8.46 (s, 2H), 9.61 (br s, 1H), 10.88 (br s, 1H); MS [M−H]−: 520.06.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-4e44db6b55154cdc88fd4000883e2b8c
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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