Diisopropylethylamine → 1-((4-Cyanophenyl)(8-methoxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 517180ノート

反応式

HRID 517180 の反応式
F[B-](F)(F)F.[CH3:6][O+](C)C.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:33]2[C:43](=[O:44])[CH2:42][C:36]3([CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH2:35][C:34]=2[OH:45])[NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)=[O:21])=[CH:14][CH:13]=1)#[N:11].C(N(CC)C(C)C)(C)C>ClCCl>[C:10]([C:12]1[CH:13]=[CH:14][C:15]([CH:18]([C:33]2[C:34](=[O:45])[CH2:35][C:36]3([CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)[CH2:42][C:43]=2[O:44][CH3:6])[NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)=[O:21])=[CH:16][CH:17]=1)#[N:11]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 867322991-((4-Cyanophenyl)(8-hydroxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea2 回

生成物 1

HCID 867323001-((4-Cyanophenyl)(8-methoxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trimethyloxonium tetrafluoroborate (320 mg, 2.16 mmol) is added to a solution of 1-((4-cyanophenyl)(8-hydroxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea (intermediate 10, 712 mg, 1.43 mmol) and N,N-diisopropylethylamine (490 μL, 2.81 mmol) in dichloromethane (20 mL). The mixture is stirred at room temperature for 30 min and washed with water. The organic layer is concentrated under reduced pressure, and the residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 380 mg; ESI mass spectrum [M+H]+=514, Retention time HPLC: 1.18 min (V012_S01).

後処理

  1. washwashed with water
  2. concentrationThe organic layer is concentrated under reduced pressure
  3. customthe residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  4. custom1.18 min (V012_S01)

出典と根拠

ORDレコード
ord-2fac46ab36e747adb8665253079ec841
出典データセット
uspto-grants-2015_08
特許番号
US09115093B2

反応ノート

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