Pyridine → 2-(Chloromethyl)-N-[6-{6-(methyloxy)-5-[(methylsulfonyl)amino]-3-pyridinyl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

HRID 1695724Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:14]([O:17][CH3:18])=[N:15][CH:16]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25].N1C=CC=CC=1.[Cl:39][CH2:40][C:41]1[S:42][CH:43]=[C:44]([C:46](Cl)=[O:47])[N:45]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:39][CH2:40][C:41]1[S:42][CH:43]=[C:44]([C:46]([NH:1][C:2]2[CH:10]=[C:9]([C:11]3[CH:16]=[N:15][C:14]([O:17][CH3:18])=[C:13]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:12]=3)[CH:8]=[C:7]3[C:3]=2[CH:4]=[N:5][N:6]3[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[O:47])[N:45]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-[5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide (700 mg, 1.478 mmol) was dissolved in DCM (30 ml) and cooled to 0° C. before pyridine (0.179 ml, 2.217 mmol) was added. To this mixture was added 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (290 mg, 1.478 mmol) as a solution in DCM (10 ml) dropwise over 15 mins. The mixture was stirred at 0° C. for 30 min. Saturated aqueous sodium bicarbonate solution (20 ml) was added to the mixture and it was stirred vigorously for 10 mins. The organic layer was separated using a hydrophobic frit, washed with water (20 ml) and concentrated in vacuo to give the title compound as an orange solid (697 mg).

Workup

additionwas added
stirringwas stirred vigorously for 10 mins
customThe organic layer was separated
washwashed with water (20 ml)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-25d41b9840934539bf364cc6e8d7e7a9
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163743B2

Reaction notes

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