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Water → HCID 10001356, 화합물

HRID 1984256
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HRID 1984256 반응식
[C:1]([C:3]1[N:8]=[C:7]([N:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24]OS(C)(=O)=O)=[CH:18][CH:17]=2)[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[CH:5][N:4]=1)#[N:2].[C:30]([C:32]1[N:37]=[C:36]([N:38]([CH2:44][C:45]2[CH:50]=[CH:49][C:48]([CH:51]([CH3:58])[CH2:52][O:53][S:54]([CH3:57])(=[O:56])=[O:55])=[CH:47][CH:46]=2)[CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH:35]=[CH:34][N:33]=1)#[N:31].O>CN(C=O)C>[CH3:12][C:11]([CH3:14])([CH3:13])[CH2:10][N:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N:38]2[CH2:44][CH2:45][CH2:50][CH2:49][CH2:48]2)=[CH:18][CH:17]=1)[C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1]#[N:2])[N:8]=1.[C:30]([C:32]1[N:37]=[C:36]([N:38]([CH2:44][C:45]2[CH:46]=[CH:47][C:48]([CH:51]([CH3:58])[CH2:52][O:53][S:54]([CH3:57])(=[O:55])=[O:56])=[CH:49][CH:50]=2)[CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH:35]=[CH:34][N:33]=1)#[N:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 962WaterHCID 57714114HCID 57714114, 화합물HCID 57714121HCID 57714121, 화합물

생성물 2

HCID 10001356HCID 10001356, 화합물HCID 57714114HCID 57714114, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of methanesulfonic acid 3-(4-{[(2-cyano-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amino]-methyl}-phenyl)-propyl ester and methanesulfonic acid 2-(4-{[(2-cyano-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amino]-methyl}-phenyl)-propyl ester (in ratio of 3:1) (130 mg, 0.31 mmoles) is dissolved in 3 ml of DMF and 1-piperizine (0.06 ml, 0.64 mmoles) is added at rt. The mixture is stirred at rt for overnight. Water is added and the organic layer is extracted with AcOEt, dried over magnesum sulfate and concentrated. The crude product is purified by silica gel column chromatography to give 56 mg of desired 4-{(2,2-dimethyl-propyl)-[4-(3-piperidin-1-yl-propyl)-benzyl]-amino}-pyrimidine-2-carbonitrile (A) in 56% yield and 24 mg of desired methanesulfonic acid 2-(4-{[(2-cyano-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amino]-methyl}-phenyl)-propyl ester (B) in 18% yield.

후처리

  1. extractionthe organic layer is extracted with AcOEt
  2. dry with materialdried over magnesum sulfate
  3. concentrationconcentrated
  4. customThe crude product is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-aa5c87cb760c4f89a7fc751be0f468c7
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07544688B2

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