Trimethylaluminum → HCID 178422737, compound

HRID 1898468Notes

Reaction equation

HRID 1898468 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[NH:10][C:11]2[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[C:15]([C:23](OC)=[O:24])=[CH:14][C:12]=2[N:13]=1.[CH:28]1([C:31]2[CH:32]=[CH:33][C:34]([F:38])=[C:35]([CH:37]=2)[NH2:36])[CH2:30][CH2:29]1.C[Al](C)C>C1(C)C=CC=CC=1>[CH:28]1([C:31]2[CH:32]=[CH:33][C:34]([F:38])=[C:35]([NH:36][C:23]([C:15]3[C:16]4[O:20][C:19]([CH3:22])([CH3:21])[CH2:18][C:17]=4[C:11]4[NH:10][C:9]([NH:8][C:7]5[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=5[Cl:27])=[N:13][C:12]=4[CH:14]=3)=[O:24])[CH:37]=2)[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 675036775-Cyclopropyl-2-fluoroanilineHCID 178496992HCID 178496992, compound

Product 1

HCID 178422737HCID 178422737, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure described for Example-137 by using methyl 2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylate (Step-1 of Intermediate-3, 0.100 g, 0.245 mmol), 5-cyclopropyl-2-fluoroaniline (0.053 g, 0.357 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL), dry toluene (5.0 mL) at room temperature to afford 0.075 g of the desired product. 1HNMR (DMSO-d6): δ 0.62 (d, J=6.3 Hz, 2H), 0.95 (d, J=8.4 Hz, 2H), 1.55 (s, 6H), 1.91 (m, 1H), 3.09 (s, 2H), 6.82 (m, 1H), 7.17 (t, J=10.5 Hz, 1H), 7.30 (s, 1H), 8.19 (d, J=5.7 Hz, 1H), 8.45 (s, 2H), 9.95 (s, 1H), 10.99 (s, 1H), 11.56 (br s, 1H); MS [M+H]+: 526.12.

Workup

  1. customThe title compound was prepared
  2. customat room temperature

Sources & evidence

ORD record
ord-98b36f81df204e6995b7e87c4f767099
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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