Water → HCID 60198395, compound

HRID 2279471Notes

Reaction equation

HRID 2279471 reaction equation
[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]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86705484HCID 86705484, compound

Product 1

HCID 60198395HCID 60198395, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-b5b8c0bdfb8b40a09bc2c6f98826748a
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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