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Diisopropylethylamine → (R,E)-1-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)-4-(cyclobutyl(methyl)amino)but-2-en-1-one

HRID 2280252
ノート
印刷プレビュー

反応式

HRID 2280252 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[N:18][C:19]=3[NH2:21])[N:14]([C@@H:22]3[CH2:26][CH2:25][NH:24][CH2:23]3)[N:13]=2)=[CH:8][CH:7]=1.Cl.[CH:31]1([N:35]([CH3:42])[CH2:36]/[CH:37]=[CH:38]/[C:39](O)=[O:40])[CH2:34][CH2:33][CH2:32]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC>[NH2:21][C:19]1[N:18]=[CH:17][N:16]=[C:15]2[N:14]([C@@H:22]3[CH2:26][CH2:25][N:24]([C:39](=[O:40])/[CH:38]=[CH:37]/[CH2:36][N:35]([CH:31]4[CH2:34][CH2:33][CH2:32]4)[CH3:42])[CH2:23]3)[N:13]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][C:4]4[CH:27]=[CH:28][CH:29]=[C:2]([F:1])[CH:3]=4)=[CH:7][CH:8]=3)[C:20]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71209019(R)-3-(4-(3-fluorophenoxy)phenyl)-1-(pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 71209048(E)-4-(cyclobutyl(methyl)amino)but-2-enoic acid hydrochloride

生成物 1

HCID 71208320
(R,E)-1-(3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)-4-(cyclobutyl(methyl)amino)but-2-en-1-one
収率 17.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4a (134 mg, 0.344 mmol), (E)-4-(cyclobutyl(methyl)amino)but-2-enoic acid hydrochloride (0.344 mmol) and HATU (122 mg, 0.38 mmol) in DMF (1.5 ml) was dropwise added DIPEA (134 mg, 1.032 mmol) at rt. Stirring was continued for 30 min at rt (monitored by HPLC). The reaction mixture was diluted with EA, washed with water and brine, and dried over sodium sulfate. Filtration followed by concentration under reduced pressure provided a residue which was purified by flash chromatography using silica gel (1-12% MeOH/DCM) to give 32 mg of the title compound (4b). MS (ESI) m/e (M+1H)+: 542.1.

後処理

  1. customat rt
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration
  5. concentrationfollowed by concentration under reduced pressure
  6. customprovided a residue which
  7. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-1b68c5b88d2c411886d17d40a679da29
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09138436B2

反応ノート

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