Acetyl chloride → HCID 86662641, compound

HRID 38841Notes

Reaction equation

HRID 38841 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.[C:37](Cl)(=[O:39])[CH3:38]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])=[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:23])=[O:24])=[C:15]([C:32]3[O:39][C:37]([CH3:38])=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 178427404HCID 178427404, compound

Product 1

HCID 86662641HCID 86662641, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

N-{2-Chloro-5-[1-[(4-methylphenyl)sulfonyl]-4-(1H-tetrazol-5-yl)-1H-indazol-6-yl]-3-pyridinyl}methanesulfonamide (50 mg, 0.092 mmol) and acetyl chloride (8.48 μl, 0.119 mmol) were placed in toluene (2 ml) and left to stand for 10 mins before heating under microwave irradiation at 120° C. for 40 mins. Additional acetyl chloride (8.48 μl, 0.119 mmol) was added and the reaction mixture heated for a further 40 mins at 120° C. The solvent was removed and the residue purified by column chromatography, on a silica cartridge (20 g) eluting with 0-100% ethyl acetate/cyclohexane followed by 0-20% methanol to give the title compound as a white solid (16 mg).

Workup

  1. waitleft
  2. temperaturethe reaction mixture heated for a further 40 mins at 120° C
  3. customThe solvent was removed
  4. customthe residue purified by column chromatography, on a silica cartridge (20 g)
  5. washeluting with 0-100% ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-93bb02b2913d40b9a8197f60e2a913cc
Source dataset
uspto-grants-2013_09
Patent number
US08524751B2

Reaction notes

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