1,2-Dichloroethane → tert-butyl (1S,3R,5S)-3-(3-(2-bromothiazole-4-carboxamido)pyridin-4-yl)-5-methylcyclohexylcarbamate

HRID 73606노트

반응식

HRID 73606 반응식
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C@@H:8]1[CH2:13][C@H:12]([CH3:14])[CH2:11][C@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1.[Br:23][C:24]1[S:25][CH:26]=[C:27]([C:29](O)=[O:30])[N:28]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[Br:23][C:24]1[S:25][CH:26]=[C:27]([C:29]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C@@H:8]2[CH2:13][C@H:12]([CH3:14])[CH2:11][C@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]2)=[O:30])[N:28]=1

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acidHCID 68919823tert-Butyl [(1S,3R,5S)-3-(3-aminopyridin-4-yl)-5-methylcyclohexyl]carbamate

생성물 1

HCID 59455711tert-butyl (1S,3R,5S)-3-(3-(2-bromothiazole-4-carboxamido)pyridin-4-yl)-5-methylcyclohexylcarbamate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution containing 1 eq each of tert-butyl (1S,3R,5S)-3-(3-aminopyridin-4-yl)-5-methylcyclohexylcarbamate, 2-bromothiazole-4-carboxylic acid, HOAT and EDC in DMF, at a concentration of 0.3 M, was stirred for 17 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 tert-butyl (1S,3R,5S)-3-(3-(2-bromothiazole-4-carboxamido)pyridin-4-yl)-5-methylcyclohexylcarbamate, LCMS (m/z): 495.1/497.1 (MH+); LC Rt=3.17 min.

후처리

  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

출처 및 근거

ORD 기록
ord-f66e730a411c4277afd9001dc93dc902
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829193B2

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