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 1185062Notes

Reaction equation

HRID 1185062 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2C=CN=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH3:17][N:18]1[CH2:23][CH2:22]C2N=C(N)[S:26][C:20]=2[CH2:19]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:26][C:20]3[CH2:19][N:18]([CH3:17])[CH2:23][CH2:22][C:13]=3[N:12]=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 580440945-bromo-1-methyl-3-(pyrimidin-4-ylamino)pyridin-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 compound 113a and starting with 115a (4.0 g, 23.5 mmol) and 3,5-dibromo-1-methylpyridin-2(1H)-one (3.0 g, 17.8 mmol) afforded 115b as a yellow solid (2.8 g, 44%). MS: [M+H]+ 357.

Sources & evidence

ORD record
ord-92be5fd1f7d34de5994c4cae2399674e
Source dataset
uspto-grants-2014_03
Patent number
US08669251B2

Reaction notes

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