Hydrochloric Acid → 1-((3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)methyl)azetidin-3-ol

HRID 539897노트

반응식

HRID 539897 반응식
[CH3:1][C:2]1[C:6](C=O)=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH3:25])[CH:20]=[CH:19]4)[N:10]=2)[N:3]=1.Cl.[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30]C)C.[BH-](OC(C)=O)(OC(C)=O)[O:35]C(C)=O.[Na+]>ClCCl>[CH3:1][C:2]1[C:6]([CH2:30][N:29]2[CH2:27][CH:33]([OH:35])[CH2:32]2)=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH3:25])[CH:20]=[CH:19]4)[N:10]=2)[N:3]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866989873-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazole-4-carbaldehyde

생성물 1

HCID 716983751-((3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)methyl)azetidin-3-ol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a slurry of intermediate 8 (77 mg, 0.23 mmol), 3-azetidinole hydrochloride (50 mg, 2 equiv.) and triethylamine (30 mL, 1 equiv.) in 20 mL of dichloromethane, was added NaBH(OAc)3 (146 mg, 3 equiv.) at room temperature. The reaction was stirred for 15 hour at room temperature and then quenched with 1N—NaOH. It was extracted with ethyl acetate and washed twice with brine. The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by recrystallization in a mixture of ethyl acetate and heptanes to afford desired Compound No. 140 as a pale yellow solid (62 mg, 69%); MS (ESI) m/z 390 [M+H]+.

후처리

  1. customquenched with 1N—NaOH
  2. extractionIt was extracted with ethyl acetate
  3. washwashed twice with brine
  4. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by recrystallization in a mixture of ethyl acetate and heptanes

출처 및 근거

ORD 기록
ord-dd8714d6feb34dbc9e4ac1f73b890593
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871778B2

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