5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine → HCID 90314065, compound

HRID 1523885Notes

Reaction equation

HRID 1523885 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH2:11][CH2:12][CH2:13][S:14]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)(=[O:16])=[O:15])(=[O:10])=[O:9].[F:23][C:24]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[CH:26][C:25]=1[C:39]1[CH:40]=[N:41][C:42]([NH2:45])=[N:43][CH:44]=1>>[CH:17]1([S:14]([CH2:13][CH2:12][CH2:11][S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:28]2[CH:27]=[CH:26][C:25]([C:39]3[CH:44]=[N:43][C:42]([NH2:45])=[N:41][CH:40]=3)=[C:24]([F:23])[CH:29]=2)(=[O:10])=[O:9])(=[O:16])=[O:15])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amineHCID 90313357HCID 90313357, compound

Product 1

HCID 90314065HCID 90314065, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 1-bromo-2-((3-(cyclohexylsulfonyl)propyl)sulfonyl)benzene and 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine. MS (ESI): mass calcd. for C25H28FN3O4S2, 517.15; m/z found, 518.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.59-8.51 (d, J=1.4, 2H), 8.20-8.14 (dd, J=8.0, 1.3, 1H), 7.82-7.76 (m, 1H), 7.72-7.67 (m, 1H), 7.59-7.52 (m, 1H), 7.51-7.46 (dd, J=7.7, 1.3, 1H), 7.38-7.31 (m, 2H), 3.16-3.08 (t, J=7.5, 2H), 3.08-3.01 (t, J=7.3, 2H), 2.94-2.82 (m, 1H), 2.07-1.97 (m, 4H), 1.91-1.80 (m, 2H), 1.79-1.62 (d, J=13.0, 1H), 1.48-1.35 (m, 2H), 1.35-1.25 (m, 2H), 1.24-1.12 (m, 1H).

Sources & evidence

ORD record
ord-c1559a9715a04ec1a32eb4f80acba78f
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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