Triethylamine → HCID 57424539, compound

HRID 1093176Notes

Reaction equation

HRID 1093176 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]([CH:25]4[CH2:30][CH2:29][N:28]([CH2:31][C:32]([F:35])([F:34])[F:33])[CH2:27][CH2:26]4)[N:23]=[CH:24][C:10]=13)[CH2:2]2.C(N(CC)CC)C.ClC(Cl)(O[C:47](=[O:53])OC(Cl)(Cl)Cl)Cl.[CH:55]1([NH2:58])[CH2:57][CH2:56]1>ClCCl>[CH:55]1([NH:58][C:47]([NH:19][C:18]2[CH:20]=[CH:21][C:15]([C:13]3[N:12]=[C:11]4[N:22]([CH:25]5[CH2:26][CH2:27][N:28]([CH2:31][C:32]([F:34])([F:35])[F:33])[CH2:29][CH2:30]5)[N:23]=[CH:24][C:10]4=[C:9]([N:3]4[CH2:4][CH:5]5[O:8][CH:1]([CH2:7][CH2:6]5)[CH2:2]4)[N:14]=3)=[CH:16][CH:17]=2)=[O:53])[CH2:57][CH2:56]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 94429TriphosgeneHCID 66589022HCID 66589022, compound

Product 1

HCID 57424539HCID 57424539, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline (47 mg, 0.097 mmol) in dichloromethane (3 mL) was treated with triethylamine (0.13 mL), followed by triphosgene (14 mg, 0.048 mmol). After the passage of five minutes, cyclopropylamine (0.14 mL) was added. The mixture was concentrated to dryness under reduced pressure. The resultant residue was purified via reverse-phase high performance liquid chromatography using a Phenomenex Gemini 21 mm×100 mm column, running a gradient elution of 10% acetonitrile/90% of 0.1% aqueous trifluoroacetic acid to 75% acetonitrile over 30 minutes. After the concentration of fractions under reduced pressure, 1-cyclopropyl-3-(4-{4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}phenyl)urea (67 mg) was obtained. MS (ES+): 571.5, 572.5 (M+H)+

Workup

  1. concentrationThe mixture was concentrated to dryness under reduced pressure
  2. customThe resultant residue was purified via reverse-phase high performance liquid chromatography
  3. washa gradient elution of 10% acetonitrile/90% of 0.1% aqueous trifluoroacetic acid to 75% acetonitrile over 30 minutes

Sources & evidence

ORD record
ord-bd30d534c1b743c7acaf28f57f282d6c
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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