Water → HCID 90310865, compound

HRID 927228Notes

Reaction equation

HRID 927228 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH:10]([C:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]=1[NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1)[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[Cl:19].[C:37](N1C=CN=C1)(N1C=CN=C1)=[O:38].O>C(#N)C.ClCCl>[Cl:19][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:11]=1[CH:10]1[NH:9][C:37](=[O:38])[N:26]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=2)[C:21]2[CH2:22][CH2:23][C:24](=[O:25])[C:20]1=2)[C:15]#[N:16]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 90311016HCID 90311016, compound2×

Product 1

HCID 90310865HCID 90310865, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.38 mL, 2.70 mmol) is added to a mixture of 4-(amino(5-oxo-2-(3-(tri-fluoromethyl)phenylamino)cyclopent-1-enyl)methyl)-3-chlorobenzonitrile hydrochloride (intermediate 20.1, 660 mg, 1.34 mmol based on 90% purity) and 1,1′-carbonyldiimidazole (270 mg, 1.68 mmol) in acetonitrile (5 mL), and the mixture is stirred at room temperature over night. Water and dichloromethane are added, and the phases are separated. The organic layer is concentrated under reduced pressure and purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 290 mg. ESI mass spectrum: [M+H]+=432; Retention time HPLC: 0.61 min (X012_S01).

Workup

  1. customthe phases are separated
  2. concentrationThe organic layer is concentrated under reduced pressure
  3. custompurified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  4. custom0.61 min (X012_S01)

Sources & evidence

ORD record
ord-9391b355aeb649b0915e11d9dfd1e05e
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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