Water → HCID 90311111, compound

HRID 927226Notes

Reaction equation

HRID 927226 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[Br:19].[C:37](N1C=CN=C1)(N1C=CN=C1)=[O:38].O>C(#N)C>[Br: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

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 90310973HCID 90310973, compound2×

Product 1

HCID 90311111HCID 90311111, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (0.43 mL, 3.0 mmol) is added to a mixture of 4-(amino(5-oxo-2-(3-(tri-fluoromethyl)phenylamino)cyclopent-1-enyl)methyl)-3-bromobenzonitrile hydrochloride (intermediate 20, 5.90 g, 12.1 mmol) and 1,1′-carbonyldiimidazole (2.46 g, 15.2 mmol) in acetonitrile (60 mL), and the mixture is stirred at room temperature over night. Water (700 mL) is added and the precipitate is filtered, washed with water and dried. Yield: 5.45 g. ESI a) mass spectrum: [(79Br)-M+H]+=476, [(81Br)-M+H]+=478; Retention time HPLC: 1.10 min (X011_S01).

Workup

  1. filtrationthe precipitate is filtered
  2. washwashed with water
  3. customdried
  4. custom1.10 min (X011_S01)

Sources & evidence

ORD record
ord-e65b4457873f4275afc1dfa17d2508ce
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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