4-Methylmorpholine → 4-[2-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1963094노트

반응식

HRID 1963094 반응식
[F:1][C:2]1[C:3]([CH3:27])=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][C:6]1[C:7]([C:21](O)=[O:22])=[C:8]2[N:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:12]=[CH:11][CH:10]=[CH:9]2.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([C:21]([C:7]2[C:6]([CH2:5][C:4]3[CH:24]=[CH:25][CH:26]=[C:2]([F:1])[C:3]=3[CH3:27])=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[CH:12]3)=[O:22])[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 677747302-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carboxylic acid

생성물 1

HCID 677724864-[2-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester수율 85.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the crude compound obtained in step 4 (125 mg, 0.35 mmol), 1-tert-butoxycarbonyl-piperazine (67.9 mg, 0.37 mmol), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (73.4 mg, 0.38 mmol) and 1-hydroxybenzotriazole (61.3 mg, 0.40 mmol) in DMF (2 ml) was added N-methyl-morpholine (0.115 ml, 1.04 mmol). The mixture was stirred at room temperature overnight, then quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (HEP/EA) to give 158 mg of the title compound.

후처리

  1. customquenched with water
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (HEP/EA)

출처 및 근거

ORD 기록
ord-b35b62629c9649289ce1f14c0245c87b
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415336B2

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