1,2-Dichloroethane → Tert-butyl 6-(3-(6-bromopicolinamido)pyridin-4-yl)-2-(trifluoromethyl)pyrimidin-4-ylcarbamate

HRID 69960

Reaction equation

HRID 69960 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=1.[Br:26][C:27]1[N:32]=[C:31]([C:33](O)=[O:34])[CH:30]=[CH:29][CH:28]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN1C(=O)CCC1>[Br:26][C:27]1[N:32]=[C:31]([C:33]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C:8]2[N:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[N:11]=[C:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[CH:9]=2)=[O:34])[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 5939196-Bromopyridine-2-carboxylic acidHCID 69047673Tert-butyl 6-(3-aminopyridin-4-yl)-2-(trifluoromethyl)pyrimidin-4-ylcarbamate

Product 1

HCID 86669205Tert-butyl 6-(3-(6-bromopicolinamido)pyridin-4-yl)-2-(trifluoromethyl)pyrimidin-4-ylcarbamateYield 95%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Method 27 was followed using tert-butyl 6-(3-aminopyridin-4-yl)-2-(trifluoromethyl)pyrimidin-4-ylcarbamate (1.0 equiv.), 6-bromopicolinic acid (1.0 equiv.), EDC (1.0 equiv.), and HOAt (1.0 equiv.) in NMP yielding tert-butyl 6-(3-(6-bromopicolinamido)pyridin-4-yl)-2-(trifluoromethyl)pyrimidin-4-ylcarbamate>95% yield. LCMS (m/z): 539/541 (MH+); LC Rt=3.97 min.

Sources & evidence

ORD record
ord-77a9c755f159463dbd057e9c4fac2105
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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