1,2-Dichloroethane → (S)-tert-butyl 1-(3-(2-bromothiazole-4-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate

HRID 1920242Notes

Reaction equation

HRID 1920242 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9]1.[Br:22][C:23]1[S:24][CH:25]=[C:26]([C:28](O)=[O:29])[N:27]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[Br:22][C:23]1[S:24][CH:25]=[C:26]([C:28]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:9]2)=[O:29])[N:27]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acidHCID 59332360(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamate

Product 1

HCID 58182192(S)-tert-butyl 1-(3-(2-bromothiazole-4-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution containing 1 eq each of (S)-tert-butyl 1-(3-aminopyridin-4-yl)piperidin-3-ylcarbamate, 2-bromothiazole-4-carboxylic acid, HOAT and EDC in DMF, at a concentration of 0.5 M, was stirred for 60 hours. The solution was diluted with EtOAc and was washed with H2O (4×), NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding (S)-tert-butyl 1-(3-(2-bromothiazole-4-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate, LCMS (m/z): 416.1 (MH+); LC Rt=1.95 min.

Workup

  1. washwas washed with H2O (4×), NaCl(sat.)
  2. dry with materialwas dried over MgSO4
  3. filtrationwas filtered
  4. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-0533594bf26b46d886b01c647ae8df26
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

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