Isopropanol → HCID 86614787, compound

HRID 1853438Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][S:16]([NH:19][CH2:20][C:21]#[CH:22])(=[O:18])=[O:17])=[CH:11][CH:10]=2)[C:5]([F:23])=[CH:4][N:3]=1.[NH2:24][C:25]1[CH:26]=[C:27]([S:31]([NH2:34])(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1.FC(F)(F)C(O)=O.CC(O)C>Cl>[NH2:34][S:31]([C:27]1[CH:26]=[C:25]([NH:24][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([CH2:15][S:16]([NH:19][CH2:20][C:21]#[CH:22])(=[O:18])=[O:17])=[CH:11][CH:10]=3)[C:5]([F:23])=[CH:4][N:3]=2)[CH:30]=[CH:29][CH:28]=1)(=[O:32])=[O:33]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-5-fluoro-N4-[4-(prop-2-ynylaminosulfonylmethyl)phenyl]-4-pyrimidineamine (34 mg, 0.096 mmol), 3-aminobenzenesulfonamide (33 mg, 0.19 mmol), and trifluoroacetic acid (11 μL, 0.14 mmol) were combined with iPrOH (0.40 mL) in a sealed vial and heated at 100° C. for 4 h. The reaction mixture was cooled to room temperature and diluted with 1N HCl (80 mL). The crude product was isolated by filtration. Further purified by column chromatography (silica gel, dichloromethane ramped to methanol:dichloromethane (3:100)) provided N2-(3-aminosulfonylphenyl)-5-fluoro-N4-[4-(prop-2-ynylaminosulfonylmethyl)phenyl]-2,4-pyrimidinediamine (I-4) as an off-white solid. 1H NMR (DMSO-d6): δ 9.57 (s, 1H), 9.47 (s, 1H), 8.15-8.08 (m, 2H), 7.99-7.95 (m, 1H), 7.84 (d, J=8.4 Hz, 2H), 7.62 (t, J=5.7 Hz, 1H), 7.43-7.32 (m, 4H), 7.26 (s, 2H), 4.35 (s, 2H), 3.79-3.75 (m, 2H), 3.35 (t, J=2.4 Hz, 1H); LCMS: purity: 96%; MS (m/e): 492 (MH+).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe crude product was isolated by filtration
customFurther purified by column chromatography (silica gel, dichloromethane ramped to methanol:dichloromethane (3:100))

Sources & evidence

ORD record: ord-b3d3a9cbbd6745cea396d50af55d0e1f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962643B2

Reaction notes

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