Triethylamine → 3-Bromo-4-[2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-benzonitrile

HRID 59654Notes

Reaction equation

HRID 59654 reaction equation
[NH2:1][CH:2]([C:12]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[Br:11].C(N(CC)CC)C.[C:37](N1C=CN=C1)(N1C=CN=C1)=[O:38]>C(#N)C>[Br:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[CH:2]1[C:12]2[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]=2[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)[C:37](=[O:38])[NH:1]1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 1186921354-{Amino-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-3-bromo-benzonitrile2×

Product 1

HCID 1186921683-Bromo-4-[2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-{Amino-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-3-bromo-benzonitrile (INTERMEDIATE 21, 16.5 g, 33 mmol) is suspended in acetonitrile (150 mL) and triethylamine (3.47 mL, 24.7 mmol) and 1,1′-carbonyldiimidazole (6.7 g, 41.2 mmol) are added. The mixture is stirred at room temperature for 1 h. The solvent is evaporated under reduced pressure and water is added. The product precipitates; the precipitate is filtered off, washed with water and dried. Yield: 14 g. ESI mass spectrum: [M+H]+=490 (bromine isotope pattern); Retention time HPLC: 0.64 min (X012_S02).

Workup

  1. customThe solvent is evaporated under reduced pressure and water
  2. additionis added
  3. customThe product precipitates
  4. filtrationthe precipitate is filtered off
  5. washwashed with water
  6. customdried
  7. custom0.64 min (X012_S02)

Sources & evidence

ORD record
ord-d32d76344d714ac5b53f227c6ad3113c
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Reaction notes

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