Morpholine → N-(4-Fluoro-benzyl)-4-(3-morpholin-4-yl-indazole-1-sulfonyl)-benzamide

HRID 1178963Notes

Reaction equation

Cl[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:30]=[CH:29][C:17]([C:18]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[O:19])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:3]=1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CCOC(C)=O>[F:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][NH:20][C:18](=[O:19])[C:17]2[CH:29]=[CH:30][C:14]([S:11]([N:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:2]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[N:3]3)(=[O:13])=[O:12])=[CH:15][CH:16]=2)=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Dissolve 4-(3-chloro-indazole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide (91 mg, 0.20 mmol) in morpholine (1.0 mL) and stir at 100° C. overnight. Dilute the solution with EtOAc (30 mL) and wash with 1N HCl (11 mL), water (10 mL), and satd NaHCO3 (10 mL). Dry, filter and concentrate the organic solution and purify the residue by flash chromatography, using a linear gradient of 20% to 80% EtOAc/hexanes, to give the title compound as a white foam (17 mg, 34%). MS (ES) 495.0 (M+1)+, 493.1 (M−1)−.

Workup

washwash with 1N HCl (11 mL), water (10 mL), and satd NaHCO3 (10 mL)
customDry
filtrationfilter
concentrationconcentrate the organic solution
custompurify the residue by flash chromatography

Sources & evidence

ORD record: ord-0c7b099eb18940feb52774dad94d450e
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276516B2

Reaction notes

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