Hydrochloric Acid → [6-(3-Quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)-pyridin-2-yl]-methanol

HRID 8274

반응식

HRID 8274 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[C:12]([C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[C:13]3[CH2:18][CH2:17][CH2:16][N:14]3[N:15]=2)[N:6]=1)=O.[BH4-].[Li+].Cl>CO>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]([C:12]2[C:11]([C:7]3[N:6]=[C:5]([CH2:3][OH:2])[CH:10]=[CH:9][CH:8]=3)=[N:15][N:14]3[CH2:16][CH2:17][CH2:18][C:13]=23)=[CH:20][CH:21]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydride2회HCID 66678270Methyl 6-(3-(quinolin-4-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)picolinate

생성물 1

HCID 10154449[6-(3-Quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)-pyridin-2-yl]-methanol수율 58.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 6-(3-quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)pyridine-2-carboxylic acid methyl ester (0.550 g, 1.48 mmol) in methanol (20 mL) is added lithium borohydride (35.5 mg, 1.63 mmol). The mixture is stirred 1 h, additional lithium borohydride (35.5 mg, 1.63 mmol) added, and the resulting mixture stirred at room temperature for 16 h. 4 N Hydrochloric acid (3 mL) is added slowly and the resulting mixture concentrated in vacuo. The residue is taken up in methanol (10 mL) and partitioned between ethyl acetate (150 mL) and saturated potassium carbonate (150 mL). The organic portion is washed with brine (150 mL), dried (magnesium sulfate), and a concentrated in vacuo. The residue is precipitated from ethyl acetate with hexanes to yield 296 mg (58%) of the title compound.

후처리

  1. stirringthe resulting mixture stirred at room temperature for 16 h
  2. concentrationthe resulting mixture concentrated in vacuo
  3. custompartitioned between ethyl acetate (150 mL) and saturated potassium carbonate (150 mL)
  4. washThe organic portion is washed with brine (150 mL)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationa concentrated in vacuo
  7. customThe residue is precipitated from ethyl acetate with hexanes

출처 및 근거

ORD 기록
ord-01768c0751dd480d88612be8046d10c7
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087626B2

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