HCID 90312288, compound → HCID 90314506, compound

HRID 1523882Notes

Reaction equation

HRID 1523882 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:14][C:13]([C:16]([F:19])([F:18])[F:17])([OH:15])[CH2:12]1)(=[O:10])=[O:9].[F:20][C:21]1[CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=[CH:23][C:22]=1[C:36]1[CH:37]=[N:38][C:39]([NH2:42])=[N:40][CH:41]=1>>[NH2:42][C:39]1[N:40]=[CH:41][C:36]([C:22]2[CH:23]=[CH:24][C:25]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]([N:11]3[CH2:14][C:13]([C:16]([F:19])([F:18])[F:17])([OH:15])[CH2:12]3)(=[O:10])=[O:9])=[CH:26][C:21]=2[F:20])=[CH:37][N:38]=1

Participants

3

Reactant 2

HCID 90312288HCID 90312288, compoundHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 90314506HCID 90314506, compound

Procedure

The title compound was prepared using analogous conditions to those described in Example 6 utilizing 1-((2-bromophenyl)sulfonyl)-3-(trifluoromethyl)azetidin-3-ol 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 C20H16F4N4O3S, 468.09; m/z found, 469.0 [M+H]+. 1H NMR (600 MHz, DMSO-d6) δ 8.53-8.47 (d, J=1.4, 2H), 8.06-8.01 (dd, J=8.0, 1.3, 1H), 7.81-7.76 (m, 1H), 7.70-7.65 (m, 1H), 7.64-7.58 (m, 1H), 7.51-7.45 (m, 2H), 7.35-7.29 (dd, J=11.7, 1.8, 1H), 7.28-7.24 (dd, J=7.8, 1.7, 1H), 6.94 (s, 2H), 3.81-3.76 (d, J=9.3, 2H), 3.71-3.66 (m, 2H)

Sources & evidence

ORD record
ord-6a8cc5194f4843cbbb74b7ccc9642cf4
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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