2-Bromopyridine → HCID 11717378, compound

HRID 2219540Notes

Reaction equation

HRID 2219540 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]([C:12]2[C:17]([NH2:18])=[CH:16][CH:15]=[C:14]([CH3:19])[N:13]=2)=[O:11])[S:7][CH:8]=1.Br[C:21]1[CH:22]=[N:23][CH:24]=[N:25][CH:26]=1.BrC1C=CC=CN=1>[Pd]>[CH3:1][O:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]([C:12]2[C:17]([NH:18][C:21]3[CH:22]=[N:23][CH:24]=[N:25][CH:26]=3)=[CH:16][CH:15]=[C:14]([CH3:19])[N:13]=2)=[O:11])[S:7][CH:8]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 783445-BromopyrimidineHCID 86607588HCID 86607588, compound

Product 1

HCID 11717378HCID 11717378, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound was prepared from 3-tert-Butoxy-carbonylamino-6-methyl-pyridine-2-carboxylic acid methyl ester in accordance with the general method of example 4; step 2 using 4-Methoxymethyl-thiazol-2-ylamine (CAS: [640768-40-7]; WO 2004081001) instead of 2-chloro-4-aminopyridine to yield [2-(4-Methoxymethyl-thiazol-2-ylcarbamoyl)-6-methyl-pyridin-3-yl]-carbamic acid tert-butyl ester as an off-white gum, MS (ISP): m/e=379.4 (M+H+). Boc-deprotection as described in example 4 step 3 yielded 3-Amino-6-methyl-pyridine-2-carboxylic acid (4-methoxymethyl-thiazol-2-yl)-amide as an off-white solid, MS (ISP): m/e=279.3 (M+H+). Palladium catalysed arylation in accordance with the general method of example 20, using 5-Bromopyrimidine instead of 3 bromopyridine yielded the final compound as a light yellow solid, MS (ISP): m/e=357.1 (M+H+).

Sources & evidence

ORD record
ord-1b7875b341bf48609d40f27cd4d8ebcf
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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