Potassium Acetate → 2-((2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol

HRID 526933노트

반응식

HRID 526933 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10](B3OC(C)(C)C(C)(C)O3)=[CH:9][N:8]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1.Cl[C:31]1[N:36]=[C:35]([NH:37][CH2:38][C:39]2(O)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[C:34]([F:46])=[CH:33][N:32]=1.CC([O-])=[O:49].[K+]>CC(N(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:31]3[N:36]=[C:35]([NH:37][CH2:38][CH:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]4[OH:49])[C:34]([F:46])=[CH:33][N:32]=3)=[CH:9][N:8]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:21])=[O:22])[C:5]2=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 517044Potassium AcetateHCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 790758021-((2-Chloro-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol2회

생성물 1

HCID 672858742-((2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol

시약·촉매·용매 2

HCID 15220664Palladium--triphenylphosphane (1/1)촉매HCID 31374Dimethylacetamide용매

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온도
140 °C

실험 절차

To a degassed solution of 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (0.15 g, 0.35 mmol), 1-((2-chloro-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol, 14a, (0.09 g, 0.35 mmol) and aqueous KOAc solution (1.04 mL, of 1M solution, 1.04 mmol) in dimethylacetamide was added palladium triphenylphosphine (0.04 g, 0.03 mmol). The reaction mixture was heated at 140° C. in microwave for 15 min and then cooled to room temperature. The reaction mixture was filtered through celite, concentrated in vacuo, and the resulting crude residue was purified by by preparatory HPLC (0.1% TFA-H2O/acetonitrile) to afford the desired product, 14b: LCMS RT=2.6 (M+1) 530.3.

후처리

  1. temperaturecooled to room temperature
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationconcentrated in vacuo
  4. customthe resulting crude residue was purified by by preparatory HPLC (0.1% TFA-H2O/acetonitrile)

출처 및 근거

ORD 기록
ord-6cd869130f5b48a78af13c52c6efd5bf
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345708B2

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