Water → 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-5-methylbenzoic acid

HRID 564502

반응식

HRID 564502 반응식
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:34][CH3:35])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:30]=[C:31]([CH3:33])[CH:32]=3)[C:26]([O:28]C)=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].O.[OH-].[Li+]>O1CCCC1>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:34][CH3:35])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:30]=[C:31]([CH3:33])[CH:32]=3)[C:26]([OH:28])=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57813541Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-5-methylbenzoate

생성물 1

HCID 578133503-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-5-methylbenzoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-5-methylbenzoate (3.49 g, 7.28 mmol) was dissolved in tetrahydrofuran (THF) (90 ml) and water (30.0 ml) was added. Lithium hydroxide (0.458 g, 10.92 mmol) was added and the mixture stirred under argon at room temperature overnight. The THF was rotavaped off, and the aqueous residue was adjusted to ˜pH of 6 with 1N HCL. A white solid formed and was filtered and washed 2× with water (10 mL). This solid was dried at 50° C. in a vacuum oven for 6 h to give the title compound as a white solid. LC-MS m/z 466.0 (M+H)+, 0.73 min (ret time); mp 236-239° C.; analytical HPLC shows 97.3% purity, (ret time 10.841 min).

후처리

  1. customA white solid formed
  2. filtrationwas filtered
  3. washwashed 2× with water (10 mL)
  4. customThis solid was dried at 50° C. in a vacuum oven for 6 h

출처 및 근거

ORD 기록
ord-bb1ae5ced5654c99b7ccb7e2e875c47a
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067408B2

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