Aluminium lithium hydride → HCID 59614410, 화합물

HRID 409455노트

반응식

HRID 409455 반응식
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

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 59614359HCID 59614359, 화합물

생성물 1

HCID 59614410HCID 59614410, 화합물수율 20%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c704939dcca04982be8c855f3ff912cc
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759365B2

반응 노트

불러오는 중…