Dimethylformamide → HCID 178422806, compound

HRID 1898374Notes

Reaction equation

HRID 1898374 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.[N:32]1(OC(N(C)C)=[N+](C)C)[C:36]2[CH:37]=[CH:38][CH:39]=CC=2N=N1.CN(C=O)C.C1(CN)CC1>C1COCC1>[CH:37]1([CH2:36][NH:32][C:23]([C:15]2[C:16]3[O:20][C:19]([CH3:22])([CH3:21])[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:25])[CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 75646CyclopropanemethanamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422814HCID 178422814, compound

Product 1

HCID 178422806HCID 178422806, compoundYield 22.1%

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, 0.080 g, 0.152 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.130 g, 0.406 mmol), TEA (0.5 mL), DMF (1.0 mL), THF (5.0 mL) and 1-cyclopropylmethanamine (0.044 g, 0.406 mmol) to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 0.220 (q, J=4.5 Hz, 2H), 0.44 (q, J=6.6 Hz, 2H), 1.01 (m, 1H), 1.51 (s, 6H), 3.02 (s, 2H), 3.19 (t, J=6.0 Hz, 2H), 7.22 (s, 1H), 7.77 (s, 1H), 8.43 (s, 2H), 10.99 (s, 1H), 11.40 (s, 1H); MS [M+H]+: 446.27.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-146868d5e6484fdc963ea99cefc5aaf2
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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