Water → HCID 60198395, 화합물

HRID 2279471노트

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HRID 2279471 반응식
[N+](C1C=CC(C([O:10][C@H:11]([CH3:41])[C@H:12]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[C:31]=2[F:40])[NH:13][C:14]([N:16]2[CH2:25][CH2:24][C:23]3[CH:22]=[N:21][C:20]([NH:26][CH:27]([CH3:29])[CH3:28])=[N:19][C:18]=3[CH2:17]2)=[O:15])=O)=CC=1)([O-])=O.C([O-])([O-])=O.[K+].[K+].O>CO>[F:40][C:31]1[C:32]([C:36]([F:37])([F:38])[F:39])=[CH:33][CH:34]=[CH:35][C:30]=1[C@H:12]([NH:13][C:14]([N:16]1[CH2:25][CH2:24][C:23]2[CH:22]=[N:21][C:20]([NH:26][CH:27]([CH3:29])[CH3:28])=[N:19][C:18]=2[CH2:17]1)=[O:15])[C@H:11]([OH:10])[CH3:41]

참가 물질

5

반응물 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86705484HCID 86705484, 화합물

생성물 1

HCID 60198395HCID 60198395, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of (1S,2R)-1-(2-fluoro-3-(trifluoromethyl)phenyl)-1-(2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)propan-2-yl 4-nitrobenzoate (40 mg, 0.040 mmol) in MeOH (1 mL) was added 2M K2CO3 (40 μL, 0.079 mmol) at RT. The solution was stirred at RT for 30 min. Water was added and reaction was extracted with DCM. The organic layer was concentrated and the resulting residue was purified by reverse phase column chromatography (SP4) eluting with a MeCH/H2O gradient (5 to 95% MeCN). The recovered product was further purified by SiO2 chromatography eluting with a MeOH/EtOAc (1 to 3% MeOH) to afford 0.6 mg (3.3%) of I-19: LCMS (ACPI-pos) m/z 420.3 (M+H)+.

후처리

  1. customreaction
  2. extractionwas extracted with DCM
  3. concentrationThe organic layer was concentrated
  4. customthe resulting residue was purified by reverse phase column chromatography (SP4)
  5. washeluting with a MeCH/H2O gradient (5 to 95% MeCN)
  6. customThe recovered product was further purified by SiO2 chromatography
  7. washeluting with a MeOH/EtOAc (1 to 3% MeOH)
  8. customto afford 0.6 mg (3.3%) of I-19

출처 및 근거

ORD 기록
ord-b5b8c0bdfb8b40a09bc2c6f98826748a
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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