2'-Hydroxybenzophenone → 2-[(6-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-fluorophenyl]hex-5-ynylimino)phenylmethyl}phenol

HRID 2404491

반응식

HRID 2404491 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:25][CH:26]1[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1)[C:11]1[CH:12]=[C:13]([C:18]#[C:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[CH:14]=[CH:15][C:16]=1[F:17].C([O-])(=O)C([O-])=O.[OH:39][C:40]1[CH:53]=[CH:52][CH:51]=[CH:50][C:41]=1[C:42]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=O>C(O)C.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:25][CH:26]1[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]1)[C:11]1[CH:12]=[C:13]([C:18]#[C:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]=[C:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:41]2[CH:50]=[CH:51][CH:52]=[CH:53][C:40]=2[OH:39])[CH:14]=[CH:15][C:16]=1[F:17]

참가 물질

6

반응물 3

HCID 83482'-HydroxybenzophenoneHCID 71081OxalateHCID 668361616-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-fluorophenyl}hex-5-ynylamine

생성물 1

HCID 1363358472-[(6-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-fluorophenyl]hex-5-ynylimino)phenylmethyl}phenol

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

A mixture of 6-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-fluorophenyl}hex-5-ynylamine, oxalate (example 557, 70 mg), 2-hydroxybenzophenone (30 mg) in ethanol (4 mL) is refluxed for 4 h. The mixture is then cooled, diluted with water and extracted with ethyl acetate. Pooled extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 100/0/0 to 90/10/0.5) to afford 2-[(6-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-fluorophenyl]hex-5-ynylimino)phenylmethyl}phenol. TLC (Eluent: CH2Cl2/MeOH/NH4OH 95/5/0.5) Rf=0.15.

후처리

  1. temperatureis refluxed for 4 h
  2. temperatureThe mixture is then cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialPooled extracts are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 100/0/0 to 90/10/0.5)

출처 및 근거

ORD 기록
ord-ae4e6df297de42c5b9dd351ac59ff374
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802664B2

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