Aluminium lithium hydride → HCID 59614410、化合物

HRID 409455ノート

反応式

HRID 409455 の反応式
C[O:2][C:3]([C:5]1[C:6]([N:17]2[CH2:21][C@@H:20]([N:22]([CH2:35][C:36]3[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[C:38]([C:46]([F:49])([F:48])[F:47])[CH:37]=3)[C:23]3[N:28]=[CH:27][C:26]([C:29]4[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=4)=[CH:25][N:24]=3)[CH2:19][C@H:18]2[CH2:50][CH3:51])=[N:7][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:9][CH:10]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:48][C:46]([F:47])([F:49])[C:38]1[CH:37]=[C:36]([CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=1)[CH2:35][N:22]([C:23]1[N:28]=[CH:27][C:26]([C:29]2[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=2)=[CH:25][N:24]=1)[C@@H:20]1[CH2:21][N:17]([C:6]2[C:5]([CH2:3][OH:2])=[CH:10][N:9]=[C:8]([N:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[N:7]=2)[C@H:18]([CH2:50][CH3:51])[CH2:19]1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 59614359HCID 59614359、化合物

生成物 1

HCID 59614410HCID 59614410、化合物収率 20%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-2-piperidin-1-yl-pyrimidine-5-carboxylic acid methyl ester (250 mg, 0.33 mmol) in 1.5 mL of THF is added LAH (24 mg, 0.66 mmol). After stirred at room temperature for 3.5 hours, the reaction is quenched by Glauber's salt. The mixture is filtered on celite, and the filtrate is concentrated. The obtained residue is purified by silica gel column chromatography (eluent: hexane/EtOAc) to give [4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-2-piperidin-1-yl-pyrimidin-5-yl]-methanol (40 mg, 20% yields); ESI-MS m/z: 690 [M+1]+, Retention time 5.79 min (condition B).

後処理

  1. customthe reaction is quenched by Glauber's salt
  2. filtrationThe mixture is filtered on celite
  3. concentrationthe filtrate is concentrated
  4. customThe obtained residue is purified by silica gel column chromatography (eluent: hexane/EtOAc)

出典と根拠

ORDレコード
ord-c704939dcca04982be8c855f3ff912cc
出典データセット
uspto-grants-2014_06
特許番号
US08759365B2

反応ノート

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