Diisopropylethylamine → 2-[(2-Chloro-6-methylphenyl)amino]-7,7-dimethyl-N-[5-(trifluoromethyl)pyridin-2-yl]-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxamide

HRID 1898392Notes

Reaction equation

HRID 1898392 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([OH:26])=O)=[CH:15][C:13]=2[N:14]=1.CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:63][C:64]1[CH:69]=[CH:68][C:67]([C:70]([F:73])([F:72])[F:71])=[CH:66][N+:65]=1[O-]>[Fe].C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([NH:63][C:64]3[CH:69]=[CH:68][C:67]([C:70]([F:72])([F:71])[F:73])=[CH:66][N:65]=3)=[O:26])=[CH:15][C:13]=2[N:14]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 178425067HCID 178425067, compoundHCID 178507581HCID 178507581, compound

Product 1

HCID 1784250522-[(2-Chloro-6-methylphenyl)amino]-7,7-dimethyl-N-[5-(trifluoromethyl)pyridin-2-yl]-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxamideYield 28.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

The title compound was prepared by following the procedure described for Example-121 using 2-[(2-chloro-6-methylphenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-35, 0.200 g, 0.537 mmol), COMU (0.873 g, 1.34 mmol), DIPEA (0.173 g, 1.34 mmol) and 2-amino-5-(trifluoromethyl)pyridine 1-oxide (Intermediate-41, 0.105 g, 0.591 mmol), iron powder (0.050 g) and acetic acid (5.0 mL) to afford 0.080 g of the desired product. 1HNMR (DMSO-d6): δ 1.57 (s, 6H), 2.24 (s, 3H), 3.13 (s, 2H), 7.25-7.33 (m, 2H), 7.42 (d, J=7.5 Hz, 1H), 7.56 (s, 1H), 8.22 (d, J=8.4 Hz, 1H), 8.49 (d, J=8.7 Hz, 1H), 8.75 (s, 1H), 9.16 (m, 1H), 10.49 (s, 1H), 10.99 (s, 1H); MS [M]+: 516.06.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-932f080222ae447a8b376d0b7d9053b7
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…