5-Amino-2-methylbenzenesulfonamide → Ammonia methanol

HRID 1947611Notes

Reaction equation

C([C:5]([NH:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([NH:16][C:17]2[C:22]([F:23])=[CH:21][N:20]=[C:19](Cl)[N:18]=2)[N:9]=1)=[O:6])(C)(C)C.[NH2:25][S:26]([C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=1[CH3:36])[NH2:32])(=[O:28])=[O:27]>CO>[NH3:7].[CH3:5][OH:6].[NH2:25][S:26]([C:29]1[CH:30]=[C:31]([NH:32][C:19]2[N:18]=[C:17]([NH:16][C:10]3[N:9]=[C:8]([NH2:7])[C:13]([O:14][CH3:15])=[CH:12][CH:11]=3)[C:22]([F:23])=[CH:21][N:20]=2)[CH:33]=[CH:34][C:35]=1[CH3:36])(=[O:27])=[O:28]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N4-[2-(tert-butylcarbonyl)amino-3-methoxypyrid-6-yl]-2-chloro-5-fluoro-4-pyrimidineamine (65) (25 mg, 0.07 mmol) and 3-aminosulfonyl-4-methylaniline (15 mg) in methanol (1 mL) was shaken in a sealed tube at 100° C. for 48 h. The reaction mixture was then chromatographed (silica gel, CH2Cl2 then 2-4% 2N NH3/MeOH in CH2Cl2) to obtain N2-(3-aminosulfonyl-4-methylphenyl)-N4-(2-amino-3-methoxypyrid-6-yl)-5-fluoro-2,4-pyrimidinediamine (66). (Note: The N-tert-butylcarbonyl group was cleaved during this reaction to give free amine function). LCMS: purity: 90%; MS (m/z): 420 (MH+).

Workup

customThe reaction mixture was then chromatographed (silica gel, CH2Cl2

Sources & evidence

ORD record: ord-4b52fd6eeff44564bc378f452e290ce2
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399472B2

Reaction notes

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