Triethylamine → HCID 86732327, compound

HRID 517207Notes

Reaction equation

HRID 517207 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([N:9]2[C:18]3[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=3[CH:12]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=3[S:28]([CH3:31])(=[O:30])=[O:29])[NH:11][C:10]2=[O:32])[CH:6]=[CH:7][CH:8]=1.Cl[C:36]([O:38][C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)=[O:37].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:24]([C:23]1[CH:26]=[CH:27][C:20]([CH:12]2[C:13]3[C:14](=[O:19])[CH2:15][CH2:16][CH2:17][C:18]=3[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:33])([F:1])[F:34])[CH:4]=3)[C:10](=[O:32])[N:11]2[C:36]([O:38][C:39]2[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=2)=[O:37])=[C:21]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:22]=1)#[N:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformate2×HCID 867323284-(1-(3-(Trifluoromethyl)phenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile

Product 1

HCID 86732327HCID 86732327, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A microwave vessel is charged with a mixture of 4-(1-(3-(trifluoromethyl)phenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile (example 18, 50 mg, 0.10 mmol), 4-nitrophenyl chloroformate (31 mg, 0.15 mmol) and a tip of a spatula of 4-dimethylaminopyridine in toluene (3 mL). Triethylamine (0.1 mL) is added, and the mixture is heated in a microwave at 150° C. for 10 min. Another portion of 4-nitrophenyl chloroformate (31 mg, 0.15 mmol) is added and the mixture is heated again at 150° C. for 20 min. All volatiles are evaporated and the residue is purified by reversed phase HPLC (Agilent ZORBAX™ SB-C18, gradient of acetonitrile in water, 0.15% formic acid). Yield: 32 mg; ESI mass spectrum M+H]+=655, Retention time HPLC: 1.10 min (Z017_S04).

Workup

  1. temperaturethe mixture is heated again at 150° C. for 20 min
  2. customAll volatiles are evaporated
  3. customthe residue is purified by reversed phase HPLC (Agilent ZORBAX™ SB-C18, gradient of acetonitrile in water, 0.15% formic acid)
  4. custom1.10 min (Z017_S04)

Sources & evidence

ORD record
ord-7f652565a36249c3aaf326f98b6f2dcd
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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