Sodium Bicarbonate → tert-Butyl {4-[4-(3-bromophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-yl}carbamate

HRID 1727370노트

반응식

HRID 1727370 반응식
Br.Br[CH:3]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)=O.C1([CH2:33][CH2:34][C:35]([NH2:37])=[S:36])C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[Br:12][C:8]1[CH:7]=[C:6]([C:4]2[N:37]=[C:35]([CH2:34][CH3:33])[S:36][C:3]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=2)[CH:11]=[CH:10][CH:9]=1.[NH2:19][C:15]1[CH:14]=[C:13]([C:3]2[S:36][C:35]([CH2:34][CH3:33])=[N:37][C:4]=2[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=2)[CH:18]=[CH:17][N:16]=1

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 51507353-PhenylpropanethioamideHCID 229326522-Bromo-1-(3-bromophenyl)-2-[2-(boc-amino)-4-pyridyl]ethanone hydrocbromide

생성물 2

HCID 229326504-[4-(3-Bromophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-amine수율 8%HCID 22932827tert-Butyl {4-[4-(3-bromophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-yl}carbamate수율 27%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-bromo-1-(3-bromophenyl)-2-[2-(tert-butoxycarbonylamino)-4-pyridyl]ethanone hydrobromide (22 g, 51 mmol) in N,N,-dimethylformamide (100 mL) was added thiopropionamide (4.3 g, 49 mmol), and the mixture was stirred for 2 hours at room temperature. Into the reaction mixture was poured an aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extracts were washed with water, then, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1), then, recrystallized from hexane-ethyl acetate to obtain 4-(3-bromophenyl)-5-[2-(tert-butoxycarbonylamino)-4-pyridyl]-2-ethyl-1,3-thiazole (6.0 g, yield 27%) and 5-(2-amino-4-pyridyl)-4-(3-bromophenyl)-2-ethyl-1,3-thiazole (1.4 g, yield 8%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1)
  6. customrecrystallized from hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-df244dbe4b4645d3b895abdf2477d0b3
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495018B2

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