Dimethylformamide → HCID 178425133, compound

HRID 1898367Notes

Reaction equation

HRID 1898367 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[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]([OH:25])=O)=[CH:14][C:12]=2[N:13]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN(C=O)C.[CH3:54][C:55]1([CH3:62])[CH2:60][CH2:59][CH2:58][CH:57]([NH2:61])[CH2:56]1>C1COCC1>[Cl:26][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[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]([NH:61][CH:57]3[CH2:58][CH2:59][CH2:60][C:55]([CH3:62])([CH3:54])[CH2:56]3)=[O:25])=[CH:14][C:12]=2[N:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 157537523,3-Dimethylcyclohexan-1-amineHCID 178422814HCID 178422814, compound

Product 1

HCID 178425133HCID 178425133, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-1 using 2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-3, 0.070 g, 0.178 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.114 g, 0.355 mmol), TEA (1.0 mL), DMF (1.0 mL), THF (5.0 mL) and 3,3-dimethylcyclohexanamine (0.100 g, 0.787 mmol) to afford 0.010 g of the desired product. 1HNMR (DMSO-d6): δ 0.93 (s, 6H), 1.07-1.11 (m, 2H), 1.23-1.29 (m, 2H), 1.33 (s, 6H), 1.49-1.54 (m, 2H), 1.80 (s, 2H), 3.00 (s, 2H), 3.80 (m, 1H), 7.20 (s, 1H), 7.48 (d, J=8.4 Hz, 1H), 8.43 (s, 2H), 10.89 (s, 1H), 11.41 (s, 1H); MS [M+H]+: 502.31.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-21cb0de8582a4c759a43b23a030e0205
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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