HCID 47218163, compound → HCID 90313391, compound

HRID 1523887Notes

Reaction equation

HRID 1523887 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH2:11][C:12]1[O:16][N:15]=[C:14]([CH:17]2[CH2:19][CH2:18]2)[N:13]=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>>[CH:17]1([C:14]2[N:13]=[C:12]([CH2:11][S:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[C:25]3[CH:24]=[CH:23][C:22]([C:36]4[CH:41]=[N:40][C:39]([NH2:42])=[N:38][CH:37]=4)=[C:21]([F:20])[CH:26]=3)(=[O:10])=[O:9])[O:16][N:15]=2)[CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 47218163HCID 47218163, compoundHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 90313391HCID 90313391, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 5-(((2-bromophenyl)sulfonyl)methyl)-3-cyclopropyl-1,2,4-oxadiazole 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 C22H18FN5O3S, 451.11; m/z found, 452.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.56 (s, 1H), 7.98-7.94 (m, 1H), 7.85-7.77 (dd, J=8.2, 6.9, 1H), 7.67-7.61 (m, 1H), 7.61-7.57 (m, 1H), 7.52-7.46 (d, J=7.6, 1H), 7.39-7.35 (dd, J=7.9, 1.6, 1H), 7.35-7.31 (m, 1H), 2.05-1.94 (m, 1H), 1.04-0.94 (m, 1H), 0.79-0.72 (m, 1H).

Sources & evidence

ORD record
ord-04df37683ac8475c96fe4e64354f91ed
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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