5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine → HCID 90314381, compound

HRID 1523853Notes

Reaction equation

HRID 1523853 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:39]=[CH:38][CH:37]=[CH:36][C:26]=1[CH2:27][S:28]([N:31]1[CH2:34][CH:33]([OH:35])[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:39]=[CH:38][CH:37]=[CH:36][C:26]=3[CH2:27][S:28]([N:31]3[CH2:32][CH:33]([OH:35])[CH2:34]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 90314064HCID 90314064, compound

Product 1

HCID 90314381HCID 90314381, 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 1-((2-bromobenzyl)sulfonyl)azetidin-3-ol. MS (ESI): mass calcd. for C20H19FN4O3S, 414.12; m/z found, 414.9 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.43-8.38 (m, 1H), 8.08 (d, J=1.5, 1H), 7.95 (m, 1H), 7.68-7.60 (m, 1H), 7.49-7.41 (m, 2H), 7.39-7.28 (m, 3H), 4.45-4.36 (m, 3H), 3.79-3.70 (m, 2H), 3.67-3.59 (m, 2H).

Sources & evidence

ORD record
ord-8df94c8c59b14671bd74c3eeadd3b096
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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