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Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester

HRID 1811665
ノート
印刷プレビュー

反応式

HRID 1811665 の反応式
Cl.[Br:2][C:3]1[S:7][C:6]2=[N:8][C:9]([NH2:11])=[CH:10][N:5]2[CH:4]=1.[C:12]([O:16][C:17]([NH:19][C@H:20]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C:28](O)=[O:29])=[O:22])=[O:18])([CH3:15])([CH3:14])[CH3:13].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[C:12]([O:16][C:17](=[O:18])[NH:19][C@@H:20]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@@H:24]1[C:28](=[O:29])[NH:11][C:9]1[N:8]=[C:6]2[N:5]([CH:10]=1)[CH:4]=[C:3]([Br:2])[S:7]2)=[O:22])([CH3:15])([CH3:13])[CH3:14]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10089106(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acidHCID 672405282-Bromo-imidazo[2,1-b]thiazol-6-ylamine hydrochloride

生成物 1

HCID 86654641(S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester
収率 18%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

To a mixture of compound 11 (0.137 mmol), compound 3a (0.206 mmol), and HATU (0.206 mmol) in dimethylformamide (1.5 mL) was added TEA (0.55 mmol) dropwise. The reaction mixture was stirred at 40° C. for 4 hrs. The solvent was removed under reduced pressure and the residue dissolved in a mixture of dichloromethane/methanol (9/1). This mixture was passed through a SCX-2 column and the column was washed three times with the same eluent. The filtrate was concentrated and the residue was purified by chromatography on a silica gel column to give compound 12a as a yellow orange solid in 18% yield. MS (ESI, EI+) m/z=548.24-550.20 (MH+).

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in a mixture of dichloromethane/methanol (9/1)
  3. washthe column was washed three times with the same eluent
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-5c8ec60bddf34e5ca00606c59726545d
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08362068B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート