Dimethylformamide → HCID 178464695, compound

HRID 1898360Notes

Reaction equation

HRID 1898360 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](O)=[O:24])=[CH:14][C:12]=2[N:13]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2N=N1.C[N:50]1CCO[CH2:52][CH2:51]1.CN(C=O)C>C1COCC1>[CH:35]1([CH:51]([NH:50][C:23]([C:15]2[C:16]3[O:20][C:19]([CH3:21])([CH3:22])[CH2:18][C:17]=3[C:11]3[NH:10][C:9]([NH:8][C:7]4[C:6]([Cl:26])=[CH:5][N:4]=[CH:3][C:2]=4[Cl:1])=[N:13][C:12]=3[CH:14]=2)=[O:24])[CH3:52])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422814HCID 178422814, compound

Product 1

HCID 178464695HCID 178464695, compound

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, 0.050 g, 0.127 mmol), O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.081 g, 0.254 mmol), N-methyl morpholine (0.5 mL), DMF (1.0 mL), THF (5.0 mL) and R-(−)-1-cyclohexyl ethyl amine (0.032 g, 0.254 mmol) to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.09 (d, J=6.3 Hz, 3H), 1.14-1.23 (m, 4H), 1.40 (s, 3H), 1.48 (s, 3H), 1.52-1.63 (m, 7H), 2.72 (s, 2H), 3.84 (m, 1H), 7.21 (s, 1H), 7.62 (d, J=7.8 Hz, 1H), 8.40 (s, 2H), 11.00 (s, 2H); MS [M+H]+: 502.45.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d1c07f373c374d2ba60783a7855dc75d
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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