Methanol → Methyl{4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1h-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}carbamate

HRID 1093212Notes

Reaction equation

HRID 1093212 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=3)[N:12]=[C:11]3[N:22]([CH2:25][CH3:26])[N:23]=[CH:24][C:10]=13)[CH2:2]2.Cl[C:28](Cl)([O:30][C:31](=O)[O:32]C(Cl)(Cl)Cl)Cl.CO>ClCCl>[CH3:28][O:30][C:31](=[O:32])[NH:19][C:18]1[CH:20]=[CH:21][C:15]([C:13]2[N:12]=[C:11]3[N:22]([CH2:25][CH3:26])[N:23]=[CH:24][C:10]3=[C:9]([N:3]3[CH2:2][CH:1]4[O:8][CH:5]([CH2:6][CH2:7]4)[CH2:4]3)[N:14]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 94429TriphosgeneHCID 665889664-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline

Product 1

HCID 90794976Methyl{4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1h-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline (150 mg, 0.43 mmol) in dichloromethane (5 mL) was treated with triphosgene (64 mg, 0.21 mmol). After the passage of 5 minutes, an excess of methanol was added to the mixture. The reaction mixture was concentrated to dryness under reduced pressure. The residue was purified by reverse-phase high performance liquid chromatography using a Phenomenex Prodigy 21 mm×250 mm column, running a gradient elution of 10% acetonitrile/90% of 0.1% aqueous trifluoroacetic acid to 100% acetonitrile to provide methyl{4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}carbamate. MS (ES+): 409.0 (M+H)+

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. customThe residue was purified by reverse-phase high performance liquid chromatography
  3. washa gradient elution of 10% acetonitrile/90% of 0.1% aqueous trifluoroacetic acid to 100% acetonitrile

Sources & evidence

ORD record
ord-77129ddd9b1d4862aa59112c28e1fb8e
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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