Chloroacetyl chloride → HCID 86662638, compound

HRID 38817Notes

Reaction equation

[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][N:19]3[S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[C:15]([C:32]3[NH:36][N:35]=NN=3)[CH:14]=2)=[CH:4][N:3]=1.[Cl:37][CH2:38][C:39](Cl)=[O:40]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][N:19]3[S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[C:15]([C:32]3[O:40][C:39]([CH2:38][Cl:37])=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

N-{2-Chloro-5-[1-[(4-methylphenyl)sulfonyl]-4-(1H-tetrazol-5-yl)-1H-indazol-6-yl]-3-pyridinyl}methanesulfonamide (1.3 g, 2.385 mmol) and chloro acetylchloride (0.285 ml, 3.58 mmol) were placed in toluene (35 ml) and the mixture heated at 105° C. for 30 mins. The temperature was increased to 115° C. and the mixture heated for 1 h. The mixture was cooled to room temperature and the solvent removed in vacuo. This was purified by chromatography on a silica (100 g) cartridge eluting with 0-100% ethyl acetate in cyclohexane followed by 0-20% methanol in dichloromethane, to give the title compound as a yellow solid (0.332 g).

Workup

temperatureThe temperature was increased to 115° C.
temperaturethe mixture heated for 1 h
temperatureThe mixture was cooled to room temperature
customthe solvent removed in vacuo
customThis was purified by chromatography on a silica (100 g) cartridge
washeluting with 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record: ord-20ca35226223450aabeaaae08daf51a7
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524751B2

Reaction notes

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