1,2-Dichloroethane → HCID 178518697, compound

HRID 843688Notes

Reaction equation

HRID 843688 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:12][CH:13]2[CH2:18][CH2:17][CH:16]([C:19](O)=[O:20])[CH2:15][CH2:14]2)[NH:3]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[F:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[CH2:39][NH2:40]>CN(C=O)C>[F:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[CH2:39][NH:40][C:19]([C@H:16]1[CH2:15][CH2:14][C@@H:13]([CH2:12][C:4]2[NH:3][C:2](=[O:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:18][CH2:17]1)=[O:20]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 666492-FluorobenzylamineHCID 181649HOAtHCID 135853157HCID 135853157, compound

Product 1

HCID 178518697HCID 178518697, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-oxo-3,4-dihydro-quinazolin-2-ylmethyl)-cyclohexanecarboxylic acid (275 mg, 1.05 mmol), EDC (200 mg, 1.05 mmol) and HOAt (142 mg, 1.05 mmol) in anhydrous DMF (4 mL) was added 2-fluorobenzylamine (131 mg, 1.05 mmol), and the resulting reaction mixture was stirred for 1 h. The reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc, and the organic layer washed 2× with water. The EtOAc was dried with MgSO4 and concentrated to give a yellow solid. Preparative chromatography eluting with chloroform:methanol gave the cis 4-(4-oxo-3,4-dihydro-quinazolin-2-ylmethyl)-cyclohexanecarboxylic acid 2-fluoro-benzylamide as a white solid: mass spectrum m/z 394 [(M+H)+; calcd for C23H24FN3O2: 393].

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc
  3. washthe organic layer washed 2× with water
  4. dry with materialThe EtOAc was dried with MgSO4
  5. concentrationconcentrated
  6. customto give a yellow solid
  7. washPreparative chromatography eluting with chloroform

Sources & evidence

ORD record
ord-c860fae19fbc4c2ca075b9b1dc0f7484
Source dataset
uspto-grants-2002_04
Patent number
US06380205B1

Reaction notes

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