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

HRID 1898485Notes

Reaction equation

HRID 1898485 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]([OH:24])=O)=[CH:21][C:11]=2[N:10]=1.[CH:28]1([CH2:31][NH2:32])[CH2:30][CH2:29]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN(C=O)C>C1COCC1>[CH:28]1([CH2:31][NH:32][C:22]([C:20]2[C:19]3[O:18][C:17]([CH3:26])([CH3:25])[CH2:16][C:15]=3[C:12]3[N:13]([CH3:14])[C:9]([NH:8][C:7]4[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=4[Cl:27])=[N:10][C:11]=3[CH:21]=2)=[O:24])[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 75646CyclopropanemethanamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67502982HCID 67502982, compound

Product 1

HCID 56968487N-(Cyclopropylmethyl)-2-((3,5-dichloropyridin-4-yl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamideYield 18.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure described for Example-1 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, 0.100 g, 0.245 mmol), cyclopropylmethanamine (0.025 g, 0.363 mmol), TBTU (0.157 g, 0.49 mmol), DMF (5 mL), THF (3 mL) to afford 0.021 g of the desired product. 1HNMR (DMSO-d6): δ 0.22 (d, J=4.2 Hz, 2H), 0.44 (d, J=6.6 Hz, 2H), 1.02 (m, 1H), 1.54 (s, 6H), 3.19 (m, 2H), 3.44 (s, 2H), 3.56 (s, 3H), 7.22 (s, 1H), 7.80 (m, 1H), 8.45 (s, 2H), 10.79 (s, 1H); MS [M+]+: 459.03.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-c45d0e1308aa4006807a53f1a6465a94
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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