Thionyl Chloride → HCID 178422804, compound

HRID 1898470Notes

Reaction equation

HRID 1898470 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl: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.S(Cl)(Cl)=O.[NH2:31][C:32]1[C:37]([F:38])=[CH:36][C:35]([Cl:39])=[CH:34][N+:33]=1[O-].CCN(C(C)C)C(C)C>C(O)(=O)C.C1COCC1>[Cl:39][C:35]1[CH:36]=[C:37]([F:38])[C:32]([NH:31][C:24]([C:16]2[C:17]3[O:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]=3[C:12]3[NH:11][C:10]([NH:9][C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[N:14][C:13]=3[CH:15]=2)=[O:25])=[N:33][CH:34]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 178422813HCID 178422813, compoundHCID 178507977HCID 178507977, compound

Product 1

HCID 178422804HCID 178422804, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the same procedure described for Example-65 by using 2-[(2,6-Dichlorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-6, 0.200 g, 0.51 mmol), thionyl chloride (1.0 mL), 2-amino-5-chloro-3-fluoropyridine 1-oxide (Intermediate-43, 0.099 g, 0.612 mmol), DIPEA (2 mL), THF (5.0 mL). To a solution of obtained crude product (0.200 g) in acetic acid (10.0 mL) was added iron powder (0.200 g). The reaction mass was stirred at 80° C. for 2-3 h. Excess of Iron powder was separated. The reaction mass was diluted with water, it was extracted with ethyl acetate. The reaction mass was filtered through celite bed and organic layer was separated, dried over anhydrous sodium sulphate and concentrated. The obtained crude was purified by column chromatography on basic alumina eluting with 1.5-2.0% MeOH:DCM to afford 0.025 g of the desired product. 1HNMR (DMSO-d6): δ 1.54 (s, 6H), 3.09 (s, 2H), 7.25 (m, 1H), 7.38 (m, 1H), 7.53 (d, J=7.8 Hz, 2H), 8.16 (d, J=9.6 Hz, 1H), 8.36 (s, 1H), 9.82 (s, 1H), 11.00 (br s, 2H); MS [M]+: 522.02.

Sources & evidence

ORD record
ord-c9c419d753644b97a1b8920b6b129343
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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