5-Bromopyridine-3-sulfonyl chloride → HCID 59532409, compound

HRID 2424637Notes

Reaction equation

HRID 2424637 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:11]([CH3:22])[CH2:10]2)=[C:4]([CH3:23])[CH:3]=1.[Br:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([S:31](Cl)(=[O:33])=[O:32])[CH:30]=1>>[Br:24][C:25]1[CH:30]=[C:29]([S:31]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C@@H:11]([CH3:22])[CH2:10]3)=[C:4]([CH3:23])[CH:3]=2)(=[O:33])=[O:32])[CH:28]=[N:27][CH:26]=1

Participants

3

Reactant 2

HCID 203244745-Bromopyridine-3-sulfonyl chlorideHCID 59262126tert-butyl (2S)-4-[(4-amino-2-methylphenyl)methyl]-2-methylpiperazine-1-carboxylate

Product 1

HCID 59532409HCID 59532409, compound

Procedure

The title compound was prepared from D7 and 3-bromopyridine-5-sulfonyl chloride using a method similar to that described for D15 except that the reaction time was overnight and column chromatography was carried out eluting with 0-100% Et2O/petroleum ether. δH (CDCl3, 400 MHz) 8.83 (1H, d), 8.80 (1H, d), 8.12 (1H, t), 7.16 (1H, d), 7.13 (1H, br.s), 6.92 (1H, d), 6.86 (1H, dd), 4.17 (1H, br.s), 3.77 (1H, d), 3.34 (2H, s), 2.99 (1H, m), 2.64 (1H, m), 2.51 (1H, d), 2.31 (3H, s), 2.14 (1H, m), 1.96 (1H, m), 1.46 (9H, s), 1.17 (3H, d). MS (ES+): MH+ 539/541.

Workup

  1. washcolumn chromatography was carried out eluting with 0-100% Et2O/petroleum ether

Sources & evidence

ORD record
ord-62e659b2f019456fa729f00a1948f78c
Source dataset
uspto-grants-2011_06
Patent number
US07964597B2

Reaction notes

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