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

HRID 1727370ノート

反応式

HRID 1727370 の反応式
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

参加物

6

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-df244dbe4b4645d3b895abdf2477d0b3
出典データセット
uspto-grants-2009_02
特許番号
US07495018B2

反応ノート

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