HCID 90312854, compound → HCID 90314046, compound

HRID 1523998Notes

Reaction equation

HRID 1523998 reaction equation
[CH3:1][N:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1)[S:3]([CH2:6][CH:7]([CH3:9])[CH3:8])(=[O:5])=[O:4].Br[C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:33]=[CH:34][C:35]([NH2:38])=[N:36][CH:37]=2)=[C:28]([F:39])[CH:27]=1>>[NH2:38][C:35]1[N:36]=[CH:37][C:32]([C:29]2[CH:30]=[CH:31][C:26]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:2]([CH3:1])[S:3]([CH2:6][CH:7]([CH3:8])[CH3:9])(=[O:4])=[O:5])=[CH:27][C:28]=2[F:39])=[N:33][CH:34]=1

Participants

3

Reactant 2

HCID 90312854HCID 90312854, compoundHCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amine

Product 1

HCID 90314046HCID 90314046, compound

Procedure

The title compound was prepared using methods analogous to those described in Step B of Example 369 using N-methyl-N-(2-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-methylpropanesulfonamide and 5-(4-bromo-2-fluoro-phenyl)pyrazin-2-amine yielding the title compound after purification by HPLC (32 mg, 41%). MS (ESI): mass calcd. C21H23FN4O2S, 414.15; m/z found, 415.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.59 (s, 1H), 8.11 (d, J=1.3, 1H), 8.04-7.94 (m, 1H), 7.47-7.37 (m, 4H), 7.36-7.31 (m, 1H), 7.30-7.24 (m, 1H), 4.69 (s, 2H), 3.13 (s, 3H), 2.70 (d, J=6.6, 2H), 2.26-2.11 (m, 1H), 1.00 (d, J=6.7, 6H).

Workup

  1. customThe title compound was prepared
  2. customafter purification by HPLC (32 mg, 41%)

Sources & evidence

ORD record
ord-0f5abbcf2a7a4da69afd45a5dfdad79d
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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