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

HRID 1524107Notes

Reaction equation

HRID 1524107 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:16]=[N:17][C:18]([NH2:21])=[N:19][CH:20]=3)=[N:13][CH:14]=2)O1.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH:33][CH2:34][C@H:35]([OH:37])[CH3:36])(=[O:32])=[O:31]>>[NH2:21][C:18]1[N:19]=[CH:20][C:15]([C:12]2[N:13]=[CH:14][C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:30]([NH:33][CH2:34][C@H:35]([OH:37])[CH3:36])(=[O:32])=[O:31])=[CH:10][CH:11]=2)=[CH:16][N:17]=1

Participants

3

Reactant 2

HCID 83029489(R)-2-bromo-N-(2-hydroxypropyl)benzenesulfonamideHCID 903141215-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidin-2-amine

Product 1

HCID 903133682-[6-(2-Aminopyrimidin-5-yl)pyridin-3-yl]-N-[(2R)-2-hydroxypropyl]benzenesulfonamide

Procedure

The title compound was prepared in a manner similar to that described in Example 427 using 5-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidin-2-amine and (R)-2-bromo-N-(2-hydroxypropyl)benzenesulfonamide. MS (ESI): mass calcd. for C18H19N5O3S, 385.12; m/z found, 386.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.92 (s, 2H), 8.60 (dd, J=2.3, 0.8, 1H), 8.09 (dd, J=8.0, 1.3, 1H), 7.91 (dd, J=8.2, 2.3, 1H), 7.82 (dd, J=8.2, 0.9, 1H), 7.70 (m, 1H), 7.62 (m, 1H), 7.41 (dd, J=7.6, 1.4, 1H), 3.70-3.59 (m, 1H), 2.79-2.67 (m, 2H), 1.04 (d, J=6.3, 3H).

Sources & evidence

ORD record
ord-0b7bdb668b1a42cea83a79dff2a1a3f6
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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