Triethylamine → N-(3,5-difluorobenzyl)-1-methyl-N-(2-{[(4S)-3-methyl-2,5-dioxo-1',3'-dihydrospiro-[imidazolidine-4,2'-inden]-5'-yl]amino}-2-oxoethyl)cyclohexanecarboxamide

HRID 386610

반응식

HRID 386610 반응식
[CH3:1][C:2]1([C:8]([OH:10])=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[Cl-].[F:25][C:26]1[CH:27]=[C:28]([CH:51]=[C:52]([F:54])[CH:53]=1)[CH2:29][NH2+:30][CH2:31][C:32]([NH:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[CH2:40][C@@:39]1([C:47](=[O:48])[NH:46][C:45](=[O:49])[N:44]1[CH3:50])[CH2:38]2)=[O:33]>C(Cl)Cl.CN(C=O)C>[F:25][C:26]1[CH:27]=[C:28]([CH:51]=[C:52]([F:54])[CH:53]=1)[CH2:29][N:30]([CH2:31][C:32]([NH:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[CH2:40][C@@:39]1([C:47](=[O:48])[NH:46][C:45](=[O:49])[N:44]1[CH3:50])[CH2:38]2)=[O:33])[C:8]([C:2]1([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:10]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 707441-Methylcyclohexanecarboxylic acidHCID 86647680N-(3,5-difluorobenzyl)-2-{[(4S)-3-methyl-2,5-dioxo-1',3'-dihydrospiro[imidazolidine-4,2'-inden]-5'-yl]amino}-2-oxoethanaminium chloride2회

생성물 1

HCID 25015785N-(3,5-difluorobenzyl)-1-methyl-N-(2-{[(4S)-3-methyl-2,5-dioxo-1',3'-dihydrospiro-[imidazolidine-4,2'-inden]-5'-yl]amino}-2-oxoethyl)cyclohexanecarboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of 1-methylcyclohexanecarboxylic acid (32.0 mg, 0.222 mmol) in DCM (1.5 mL) was added one drop of DMF (cat.), followed by oxalyl chloride (37.0 mg, 0.228 mmol), while at ambient temperature and under a constant stream of nitrogen. Upon cessation of gas evolution, the reaction mixture was cooled to 0° C. prior to the introduction of triethylamine (34.0 mg, 0.333 mmol) as a solution in DCM (2.0 mL), and then N-(3,5-difluorobenzyl)-2-{[(4S)-3-methyl-2,5-dioxo-1′,3′-dihydrospiro[imidazolidine-4,2′-inden]-5′-yl]amino}-2-oxoethanaminium chloride (50.0 mg, 0.111 mmol, Intermediate 1). After 1 hour the reaction mixture was applied directly to a silica gel column for purification, eluting with DCM:MeOH—99:1 to 95:5. Product containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=561 (M+23(Na+)). HRMS: m/z=539.2477; calculated m/z=539.2464 for C29H33N4O4F2.

후처리

  1. customAfter 1 hour the reaction mixture was applied directly to a silica gel column for purification
  2. washeluting with DCM
  3. additionProduct containing fractions
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b6955718136e40a596cd15ee41e49d7c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372859B2

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