HCID 68751162, compound → HCID 178461962, compound

HRID 1396624Notes

Reaction equation

HRID 1396624 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[N:9][C:8]([C@@H:20]([NH:22][C:23]1[N:31]=[CH:30][N:29]=[C:28]3[C:24]=1[N:25]=[CH:26][N:27]3C1CCCCO1)[CH3:21])=[C:7]2[F:38]>Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)=[N:9][C:8]([C@@H:20]([NH:22][C:23]1[N:31]=[CH:30][N:29]=[C:28]3[C:24]=1[N:25]=[CH:26][NH:27]3)[CH3:21])=[C:7]2[F:38]

Participants

3

Reactant 1

HCID 68751162HCID 68751162, compound

Product 1

HCID 178461962HCID 178461962, compound

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of N—((S)-1-(8-chloro-4-fluoro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine 84 (60 mg, 0.11 mmol) in hydrogen chloride/methanol solution (4 N, 20 mL) was stirred at RT for 0.5 h and then concentrated in vacuo. The residue was suspended in water (20 mL), neutralized with concentrated ammonium hydroxide to adjust the pH to 8-9 and then extracted with DCM (3×10 mL). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (2-10% MeOH-DCM) to afford the product (S)—N-(1-(8-chloro-4-fluoro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethyl)-9H-purin-6-amine 85. ESI-MS m/z: 456.2 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with DCM (3×10 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by flash column chromatography on silica gel (2-10% MeOH-DCM)

Sources & evidence

ORD record
ord-3cffaad64f8e438c8ce969265c010d71
Source dataset
uspto-grants-2014_12
Patent number
US08901133B2

Reaction notes

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