Triethylamine → HCID 86732383, compound

HRID 517260Notes

Reaction equation

HRID 517260 reaction equation
[H-].[Na+].C(N(CC)CC)C.[O:10]=[C:11]1[NH:20][CH:19]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[C:18]2[C:17](=[O:29])[CH2:16][CH2:15][CH2:14][C:13]=2[N:12]1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=1.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>O1CCCC1>[CH3:40][S:41]([N:20]1[CH:19]([C:21]2[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=2)[C:18]2[C:17](=[O:29])[CH2:16][CH2:15][CH2:14][C:13]=2[N:12]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:37])[F:38])[CH:31]=2)[C:11]1=[O:10])(=[O:43])=[O:42]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 86732326HCID 86732326, compound

Product 1

HCID 86732383HCID 86732383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in mineral oil, 6 mg, 0.15 mmol) and triethylamine (26 μL, 182 μmol) are added to a solution of 4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-benzonitrile (example 1, 25 mg, 61 μmol) in tetrahydrofuran (600 μL), and the mixture is stirred at room temperature for 15 min. Methanesulfonyl chloride (6 μL, 0.07 mmol) is added, and the mixture is stirred for 2.5 h and purified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 13 mg; ESI mass spectrum [M+H]+=490; Retention time HPLC: 0.95 min (Z018_S04).

Workup

  1. stirringthe mixture is stirred for 2.5 h
  2. custompurified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  3. custom0.95 min (Z018_S04)

Sources & evidence

ORD record
ord-09bc080645f242ebaaf5c86c01390eea
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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