5-Bromo-2-methanesulfonylpyridine → HCID 71487974, compound

HRID 1908686Notes

Reaction equation

HRID 1908686 reaction equation
C(O[C:5]1[N:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]([C@H:16]2[CH2:18][C@@H:17]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:15])[CH3:12])=[CH:7][CH:6]=1)(C)C.C[S:26]([C:29]1N=CC([C@@H](N)C)=C[CH:30]=1)(=[O:28])=[O:27].CS(C1N=CC(C(=O)C)=CC=1)(=O)=O.BrC1C=CC(S(C)(=O)=O)=NC=1>>[CH2:29]([S:26]([C:5]1[N:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]([C@H:16]2[CH2:18][C@@H:17]2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:15])[CH3:12])=[CH:7][CH:6]=1)(=[O:28])=[O:27])[CH3:30]

Participants

5

Reactant 4

HCID 134334245-Bromo-2-methanesulfonylpyridineHCID 68653876HCID 68653876, compoundHCID 71201914HCID 71201914, compoundHCID 84668872HCID 84668872, compound

Product 1

HCID 71487974HCID 71487974, compound

Procedure

Prepared analogously to Compound 1 using IM46 and (S)-1-(6-Methanesulfonyl-pyridin-3-yl)-ethylamine (prepared from 1-(6-Methanesulfonyl-pyridine-3-yl)-ethanone analogously to IM24, which was prepared from commercially available 5-Bromo-2-methanesulfonyl-pyridine CAS 98626-95-0). Yield from IM46=1.54 g (68%). 1H-NMR (500 MHz, DMSO) δ 8.80 (d, 1H), 8.72 (s, 1H), 8.02 (m, 2H), 7.27 (m, 2H), 7.20 (s, 1H), 7.12 (d, 2H), 5.08 (m, 1H), 3.27 (s, 3H), 2.20 (m, 1H), 1.95 (m, 1H), 1.42 (d, 3H), 1.37 (m, 1H), 1.22 (m, 1H). LC-MS (m/z) 345.1 (MH+), tR=1.21 min (method A).

Workup

  1. customYield from IM46=1.54 g (68%)

Sources & evidence

ORD record
ord-40853531d38c4ea383218bd8db2004e2
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

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