Diisopropylethylamine → 1-{5-tert-Butyl-2-[3-(tert-butyl-dimethyl-silanyloxy)-5-chloro-phenyl]-2H-pyrazol-3-yl}-3-{(1S,4R)-4-[3-((S)-1-methyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea

HRID 60662ノート

反応式

HRID 60662 の反応式
ClC(Cl)(Cl)CO[C:5](=[O:31])[NH:6][C:7]1[N:8]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH:17]=2)[N:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1.[CH3:34][N:35]1[CH2:39][CH2:38][CH2:37][C@H:36]1[C:40]1[N:44]2[CH:45]=[C:46]([O:49][C@H:50]3[C:59]4[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=4)[C@@H:53]([NH2:60])[CH2:52][CH2:51]3)[CH:47]=[CH:48][C:43]2=[N:42][N:41]=1.CCN(C(C)C)C(C)C>C1COCC1.O>[C:12]([C:10]1[CH:11]=[C:7]([NH:6][C:5]([NH:60][C@@H:53]2[C:54]3[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=3)[C@H:50]([O:49][C:46]3[CH:47]=[CH:48][C:43]4[N:44]([C:40]([C@@H:36]5[CH2:37][CH2:38][CH2:39][N:35]5[CH3:34])=[N:41][N:42]=4)[CH:45]=3)[CH2:51][CH2:52]2)=[O:31])[N:8]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([O:23][Si:24]([C:27]([CH3:28])([CH3:30])[CH3:29])([CH3:25])[CH3:26])[CH:17]=2)[N:9]=1)([CH3:15])([CH3:14])[CH3:13]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 117666105(1S,4R)-4-[3-((S)-1-Methyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-ylamineHCID 123756753{5-tert-Butyl-2-[3-(tert-butyl-dimethyl-silanyloxy)-5-chloro-phenyl]-2H-pyrazol-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester

生成物 1

HCID 1233369991-{5-tert-Butyl-2-[3-(tert-butyl-dimethyl-silanyloxy)-5-chloro-phenyl]-2H-pyrazol-3-yl}-3-{(1S,4R)-4-[3-((S)-1-methyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea収率 107.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of Intermediate 62d (193 mg, 0.35 mmol) and Intermediate E (115 mg, 0.32 mmol) and DIPEA (166 μL, 0.94 mmol) in THF (3.5 mL) was stirred at reflux for 24 h. The cooled reaction mixture was diluted with water and extracted with DCM. The combined organics were dried and concentrated in vacuo to give the title compound (265 mg, 99%). LCMS (Method 3): Rt 3.82 min, m/z 769 [MH+].

後処理

  1. temperatureat reflux for 24 h
  2. customThe cooled reaction mixture
  3. extractionextracted with DCM
  4. customThe combined organics were dried
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-15be7a23b1da461797c143608cbdbcf3
出典データセット
uspto-grants-2016_09
特許番号
US09440974B2

反応ノート

読み込み中…