5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine → HCID 90312823, compound

HRID 1523858Notes

Reaction equation

HRID 1523858 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2[O:12][C:11](C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.Br[C:25]1[CH:44]=[CH:43][CH:42]=[CH:41][C:26]=1[CH2:27][S:28]([N:31]1[CH2:36][CH2:35][CH:34]([NH:37][C:38](=[O:40])[CH3:39])[CH2:33][CH2:32]1)(=[O:30])=[O:29]>>[CH:11]([OH:12])=[O:29].[NH2:23][C:20]1[N:21]=[CH:22][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:25]3[CH:44]=[CH:43][CH:42]=[CH:41][C:26]=3[CH2:27][S:28]([N:31]3[CH2:32][CH2:33][CH:34]([NH:37][C:38](=[O:40])[CH3:39])[CH2:35][CH2:36]3)(=[O:29])=[O:30])=[CH:7][C:2]=2[F:1])=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amineHCID 90313488HCID 90313488, compound

Product 1

HCID 90312823HCID 90312823, compound

Procedure

The title compound was prepared using analogous conditions to those described in Example 1 utilizing 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrazin-2-amine and N-(1-((2-bromobenzyl)sulfonyl)piperidin-4-yl)acetamide. MS (ESI): mass calcd. for C24H26FN5O3S, 483.17; m/z found, 484.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 8.03 (d, J=1.3, 1H), 7.95 (m, 1H), 7.81 (d, J=7.3, 1H), 7.64-7.55 (m, 1H), 7.50-7.31 (m, 5H), 6.73 (s, 2H), 4.35 (s, 2H), 3.71-3.56 (m, 1H), 3.39 (d, J=11.6, 2H), 2.79 (t, J=10.8, 2H), 1.82-1.67 (m, 5H), 1.41-1.24 (m, 3H).

Sources & evidence

ORD record
ord-1a8147f8cfc74f7daad826e2098285b1
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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