Binap, (A+-)- → 4-{4-[7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 2189292노트

반응식

HRID 2189292 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].Cl[C:28]1[N:29]=[CH:30][C:31]2[CH:36]=[CH:35][N:34]([CH:37]([CH2:40][CH3:41])[CH2:38][CH3:39])[C:32]=2[N:33]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:28]3[N:29]=[CH:30][C:31]4[CH:36]=[CH:35][N:34]([CH:37]([CH2:40][CH3:41])[CH2:38][CH3:39])[C:32]=4[N:33]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 634876Binap, (A+-)-HCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylateHCID 23676156Sodium t-butoxideHCID 580159322-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 690753604-{4-[7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester수율 89.9%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매2회

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온도
100 °C

실험 절차

To a mixture of 4-(4-amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (133 mg, 0.48 mmol) and sodium tert-butoxide (57.6 mg, 0.6 mmol) in 1,4-dioxane (0.5 mL) is added a solution of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine (90 mg, 0.4 mmol) in 1,4-dioxane (1.0 mL), Pd2(dba)3 (18.3 mg, 0.02 mmol) and BINAP (25 mg, 0.04 mmol). The mixture is degassed, and heated at 100° C. for 3 h. The mixture is cooled to room temperature, diluted with EtOAc, and filtered through celite. The filtrate is concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2, EtOAc:Hexane=1:1) to give 167 mg of 4-{4-[7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester as a pale yellow solid.

후처리

  1. customThe mixture is degassed
  2. temperatureThe mixture is cooled to room temperature
  3. additiondiluted with EtOAc
  4. filtrationfiltered through celite
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customThe residue is purified by flash chromatography (SiO2, EtOAc:Hexane=1:1)

출처 및 근거

ORD 기록
ord-4316ac618800464baa98b6d2cfebf8fd
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324225B2

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