Thionyl Chloride → HCID 178425066, compound

HRID 1898469Notes

Reaction equation

HRID 1898469 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](O)=[O:25])=[CH:15][C:13]=2[N:14]=1.[NH2:27][C:28]1[C:33]([F:34])=[CH:32][C:31]([Cl:35])=[CH:30][N+:29]=1[O-].S(Cl)(Cl)=O.CCN(C(C)C)C(C)C>C(O)(=O)C.C1C=CC=CC=1>[Cl:35][C:31]1[CH:32]=[C:33]([F:34])[C:28]([NH:27][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]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[N:14][C:13]=3[CH:15]=2)=[O:25])=[N:29][CH:30]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 178425067HCID 178425067, compoundHCID 178507977HCID 178507977, compound

Product 1

HCID 178425066HCID 178425066, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

The title compound was prepared by following the same procedure described for Example-108 by 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, 0.536 mmol), 2-amino-5-chloro-3-fluoropyridine 1-oxide (Intermediate-43, 0.104 g, 0.643 mmol), thionyl chloride (2 mL), DIPEA (2 mL), benzene (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 0.021 g of the desired product. 1HNMR (DMSO-d6): 1HNMR (DMSO-d6): δ 1.52 (s, 6H), 2.23 (s, 3H), 3.10 (s, 2H), 7.23-7.31 (m, 2H), 7.40 (d, J=7.8 Hz, 1H), 7.47 (s, 1H), 8.14 (d, J=9.6 Hz, 1H), 8.33 (s, 1H), 9.07 (br s, 1H), 9.84 (s, 1H), 10.92 (brs, 1H); MS [M+H]+: 500.12.

Sources & evidence

ORD record
ord-00dee1d7aa46471c989db63841471234
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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