Dimethylformamide → HCID 178421857, compound

HRID 1898370Notes

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.CN1CCO[CH2:52][CH2:51]1.C[N:57]([CH:59]=O)C.[CH2:61]1COCC1>>[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:57][CH:59]3[CH:40]([CH3:35])[CH2:39][CH:38]4[CH2:52][CH:51]3[C:37]4([CH3:36])[CH3:61])=[O:24])=[CH:14][C:12]=2[N:13]=1

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 79724-Methylmorpholine

HCID 8028Tetrahydrofuran

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

HCID 178422814HCID 178422814, compound

Product 1

HCID 178421857HCID 178421857, compound

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, 0.121 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.081 g, 0.255 mmol), N-methyl morpholine (0.5 mL), DMF (1.0 mL), THF (5.0 mL) and 1R,2R,3R,5(−)-isopinocampheyl amine (0.039 g, 0.254 mmol) to afford 0.008 g of the desired product. 1HNMR (DMSO-d6): δ 1.03 (s, 3H), 1.08 (d, J=6.9 Hz, 3H), 1.22 (s, 6H), 1.50 (s, 7H), 1.83-1.85 (m, 2H), 1.95 (m, 1H), 3.02 (s, 2H), 4.26 (m, 1H), 7.21 (s, 1H), 7.70 (d, J=8.4 Hz, 1H), 8.43 (s, 2H), 10.91 (brs, 1H), 11.42 (s, 1H); MS [M+H]+: 528.39.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-e38a439f107e4764adb889fe883890da
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519149B2

Reaction notes

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