3-Amino-1-propanol → N-(3-hydroxypropyl)-4-({4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)benzenesulfonamide

HRID 1715692Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-({4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)benzenesulfonyl chloride (0.10 g, 0.25 mmol) in 2 ml of ethyl acetate is added 3-amino-1-propanol (0.19 g, 2.5 mmol) with stirring, at 0° C. The mixture is stirred at room temperature for 1 hr and then quenched with water (10 ml). The ethyl acetate is evaporated, the resulting suspension is filtered, and the precipitate is washed with water, and hexanes, and then dried in vacuo to give 0.10 g of a white solid; mp 204-205° C.; HRMS: calcd for C20H19F3N4O3S, 452.1130; found (ESI-FTMS, [M+H]1+), 453.12161.

Workup

stirringThe mixture is stirred at room temperature for 1 hr
customquenched with water (10 ml)
customThe ethyl acetate is evaporated
filtrationthe resulting suspension is filtered
washthe precipitate is washed with water, and hexanes
customdried in vacuo

Sources & evidence

ORD record: ord-ce82a455118041a1bba8380dca4d4443
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799915B2

Reaction notes

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