(R)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide → 2-[6-(2-Aminopyrimidin-5-yl)pyridin-3-yl]-N-[(1R)-2-hydroxy-1-methylethyl]benzenesulfonamide

HRID 1524110Notes

Reaction equation

HRID 1524110 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][C@H:34]([CH3:37])[CH2:35][OH: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][C@H:34]([CH3:37])[CH2:35][OH:36])(=[O:32])=[O:31])=[CH:10][CH:11]=2)=[CH:16][N:17]=1

Participants

3

Reactant 2

HCID 79027397(R)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamideHCID 903141215-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidin-2-amine

Product 1

HCID 903140532-[6-(2-Aminopyrimidin-5-yl)pyridin-3-yl]-N-[(1R)-2-hydroxy-1-methylethyl]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-(1-hydroxypropan-2-yl)benzenesulfonamide. MS (ESI): mass calcd. for C18H19N5O3S, 385.12; m/z found, 386.1 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.92 (s, 2H), 8.66-8.56 (m, 1H), 8.19 (dd, J=8.0, 1.4, 1H), 7.95 (dd, J=8.2, 2.3, 1H), 7.83 (dd, J=8.2, 0.9, 1H), 7.72 (m, 1H), 7.64 (m, 1H), 7.43 (dd, J=7.5, 1.4, 1H), 3.43-3.16 (m, 4H), 1.03 (d, J=6.6, 3H).

Sources & evidence

ORD record
ord-d658aff19d1a4819bdaa37786bf6ef96
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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