5-methyl-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amine → 5-Bromo-1-methyl-3-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-ylamino)pyridin-2(1H)-one

HRID 1021926Notes

Reaction equation

HRID 1021926 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14](N3CCN(C(OC(C)(C)C)=O)C[C@@H]3C)=[CH:13]C=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH3:31][N:32]1CCC2N=C(N)[S:40][C:34]=2[CH2:33]1.BrC1C(=O)N(C)C=C(Br)C=1>>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[S:40][C:34]3[CH2:33][N:32]([CH3:31])[CH2:13][CH2:14][C:15]=3[N:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 3

HCID 23979985-methyl-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amineHCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 86683729(S)-3-[[5-(4-Boc-2-methyl-1-piperazinyl)-2-pyridyl]amino]-5-bromo-1-methylpyridin-2(1H)-one

Product 1

HCID 580436615-Bromo-1-methyl-3-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-ylamino)pyridin-2(1H)-oneYield 44%

Procedure

Following the procedures described for 191g and starting with 203a (4.0 g, 23.5 mmol) and 3,5-dibromo-1-methylpyridin-2(1H)-one (3.0 g, 17.8 mmol) afforded 203b as yellow solid (2.8 g, 44%). MS: [M+H]+ 357.

Sources & evidence

ORD record
ord-d8bb88357495434582f5a24d982ddda8
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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