Diisopropylethylamine → N-(5-Chloro-3-fluoropyridin-2-yl)-2-((2-chloro-6-fluorophenyl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide

HRID 1898394Notes

Reaction equation

HRID 1898394 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F: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](O)=[O:25])=[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[C:69]([F:70])=[CH:68][C:67]([Cl:71])=[CH:66][N+:65]=1[O-]>[Fe].C(O)(=O)C.CN(C=O)C>[Cl:71][C:67]1[CH:68]=[C:69]([F:70])[C:64]([NH:63][C:24]([C:16]2[C:17]3[O:21][C:20]([CH3:22])([CH3:23])[CH2:19][C:18]=3[C:12]3[NH:11][C:10]([NH:9][C:3]4[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[N:14][C:13]=3[CH:15]=2)=[O:25])=[N:65][CH:66]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 178422815HCID 178422815, compoundHCID 178507977HCID 178507977, compound

Product 1

HCID 178422805N-(5-Chloro-3-fluoropyridin-2-yl)-2-((2-chloro-6-fluorophenyl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamideYield 13.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by following the procedure described for Example-121 using 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.200 g, 0.266 mmol), COMU (0.569 g, 0.663 mmol), DIPEA (0.732 g, 5.66 mmol), 2-amino-5-chloro-3-fluoropyridine 1-oxide (Intermediate-43, 0.095 g, 0.584 mmol), DMF (3.0 mL), iron powder (0.200 g, 3.57 mmol) and acetic acid (10.0 mL) to afford 0.018 g of the desired product. 1HNMR (DMSO-d6): δ 1.54 (s, 6H), 3.10 (s, 2H), 7.30 (m, 3H), 7.40 (m, 1H), 8.17 (d, J=9.3 Hz, 1H), 8.36 (s, 1H), 9.85 (s, 1H), 11.00 (2H); MS [M]+: 504.04.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-927cd3680ec64977a84235e828feba3c
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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