(R)-2-bromo-N-(2-hydroxypropyl)benzenesulfonamide → 2-[6-(2-Aminopyrimidin-5-yl)-5-fluoropyridin-3-yl]-N-[(2R)-2-hydroxypropyl]benzenesulfonamide

HRID 1524099Notes

Reaction equation

HRID 1524099 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11](B(O)O)=[CH:10][C:9]=2[F:17])=[CH:4][N:3]=1.Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([NH:28][CH2:29][C@H:30]([OH:32])[CH3:31])(=[O:27])=[O:26]>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:25]([NH:28][CH2:29][C@H:30]([OH:32])[CH3:31])(=[O:27])=[O:26])=[CH:10][C:9]=2[F:17])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 83029489(R)-2-bromo-N-(2-hydroxypropyl)benzenesulfonamideHCID 90313056(6-(2-Aminopyrimidin-5-yl)-5-fluoropyridin-3-yl)boronic acid

Product 1

HCID 903130932-[6-(2-Aminopyrimidin-5-yl)-5-fluoropyridin-3-yl]-N-[(2R)-2-hydroxypropyl]benzenesulfonamide

Procedure

The title compound was prepared in a manner similar to that described in Example 427 using (6-(2-aminopyrimidin-5-yl)-5-fluoropyridin-3-yl)boronic acid and (R)-2-bromo-N-(2-hydroxypropyl)benzenesulfonamide. MS (ESI): mass calcd. for C18H18FN5O3S, 403.11; m/z found, 404.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 9.02 (d, J=0.8, 2H), 8.52-8.47 (m, 1H), 8.09 (dd, J=7.9, 1.4, 1H), 7.81 (dd, J=11.9, 1.8, 1H), 7.72 (m, 1H), 7.66 (m, 1H), 7.46 (dd, J=7.5, 1.4, 1H), 3.74-3.59 (m, 1H), 2.84-2.66 (m, 2H), 1.06 (d, J=6.3, 3H).

Sources & evidence

ORD record
ord-1fdbadc43d294552a110578a75301be9
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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