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Triethylamine → 5-(6-Amino-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid [3-(4-isopropylpiperazin-1-ylmethyl)-5-trifluoromethyl-phenyl]-amide

HRID 2264596
ノート
印刷プレビュー

反応式

HRID 2264596 の反応式
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[F:13][C:14]([F:33])([F:32])[C:15]1[CH:16]=[C:17]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:24]2)[CH:18]=[C:19]([CH:21]=1)[NH2:20].CCN(CC)CC.[NH2:41][C:42]1[N:47]=[CH:46][N:45]=[C:44]([O:48][C:49]2[CH:50]=[C:51]3[C:55](=[CH:56][CH:57]=2)[NH:54][CH2:53][CH2:52]3)[CH:43]=1>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].O.CCOC(C)=O>[CH:29]([N:26]1[CH2:25][CH2:24][N:23]([CH2:22][C:17]2[CH:18]=[C:19]([NH:20][C:2]([N:54]3[C:55]4[C:51](=[CH:50][C:49]([O:48][C:44]5[CH:43]=[C:42]([NH2:41])[N:47]=[CH:46][N:45]=5)=[CH:57][CH:56]=4)[CH2:52][CH2:53]3)=[O:4])[CH:21]=[C:15]([C:14]([F:13])([F:32])[F:33])[CH:16]=2)[CH2:28][CH2:27]1)([CH3:31])[CH3:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 8471Triethylamine2 回HCID 94429TriphosgeneHCID 574314423-(4-Isopropylpiperazin-1-ylmethyl)-5-trifluoromethyl-anilineHCID 675304825-(6-amino-pyrimidin-4-yloxy)-2,3-dihydro-1H-indole

生成物 1

HCID 595964085-(6-Amino-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid [3-(4-isopropylpiperazin-1-ylmethyl)-5-trifluoromethyl-phenyl]-amide

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒

実験手順

49 mg (0.16 mMol) triphosgene are dissolved in 5 ml ice-cooled CH2Cl2. Then a solution of 149 mg (0.49 mMol) 5-trifluoromethyl-3-(4-isopropylpiperazin-1-ylmethyl)-aniline and 98 μl (0.70 mMol) Et3N in 2 ml CH2Cl2 is added during 5 min. After 3 additional minutes, the mixture is warmed up to rt by a water bath and then a solution of 0.47 mMol 5-(6-amino-pyrimidin-4-yloxy)-2,3-dihydro-1H-indole (Step 20.3) and 65 μl (0.47 mMol) Et3N in 2 ml CH2Cl2 is added during 5 min. After 2 h at rt, the mixture is diluted with sat. Na2CO3 solution/water 1:1 and EtOAc, the aqueous phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Reversed phase MPLC (Gilson system) gives the title compound: MS: [M+1]+=556; HPLC: AtRet=9.7.

後処理

  1. customthe aqueous phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-45e9f3aa833040bf9cb2ccdcb884fb62
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07855215B2

反応ノート

読み込み中…

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