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

HRID 737029

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-85b32fdc61f24de9aa5c9bed40a6d0e3
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595339B2

Linked notes

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