Diisopropylethylamine → 4-Chloro-2-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-thiazole-5-carbaldehyde

HRID 509953노트

반응식

HRID 509953 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.Cl[C:23]1[S:24][C:25]([CH:29]=[O:30])=[C:26]([Cl:28])[N:27]=1>O1CCCC1>[Cl:28][C:26]1[N:27]=[C:23]([NH:10][CH2:9][C:6]2[CH:7]=[N:8][C:3]([C:2]([F:11])([F:1])[F:12])=[CH:4][CH:5]=2)[S:24][C:25]=1[CH:29]=[O:30]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 14886722,4-Dichloro-1,3-thiazole-5-carboxaldehydeHCID 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridine

생성물 1

HCID 582590004-Chloro-2-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-thiazole-5-carbaldehyde수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of C-(6-trifluoromethyl-pyridin-3-yl)-methylamine (74, 1.0 g, 5.7 mmol) and N,N-diisopropylethylamine (2.0 mL, 11 mmol) in 100 mL of tetrahydrofuran, 2,4-dichloro-thiazole-5-carbaldehyde (73, 1.1 g, 6.2 mmol) in 10 mL of tetrahydrofuran was added dropwise at room temperature. The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (75, 1.2 g, 66%). MS (ESI)=[M+H+]+=322.11

후처리

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with ethyl acetate in hexane
  8. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-b6d9c13062344349bff0f6da4067aed1
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096593B2

반응 노트

불러오는 중…