Triethylamine → HCID 178454417, compound

HRID 538045Notes

Reaction equation

HRID 538045 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[O:21])[CH2:16][CH2:15]2)[C:3]1=[O:28].CCN(CC)CC.[C:36](Cl)(=[O:40])[CH2:37][CH2:38][CH3:39]>C(Cl)Cl>[C:36]([N:25]1[CH2:26][CH2:27][N:22]([C:20]([C@H:17]2[CH2:18][CH2:19][C@H:14]([CH2:13][N:4]3[C:5](=[O:12])[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[N:2]([CH3:1])[C:3]3=[O:28])[CH2:15][CH2:16]2)=[O:21])[CH2:23][CH2:24]1)(=[O:40])[CH2:37][CH2:38][CH3:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 178481611HCID 178481611, compound

Product 1

HCID 178454417HCID 178454417, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.26 mmol) of 1-Methyl-3-[trans-4-(piperazine-1-carbonyl)-cyclohexylmethyl]-1H-quinazoline-2,4-dione was dissolved in DCM (3 ml). 75 μL (0.52 mmol) of Et3N and then 41 μL (0.39 mmol) of butyryl chloride were added and the mixture was stirred at room temperature overnight. The solution was washed with a 0.4 M solution of Na2CO3, the organic phase was separated and dried over Na2SO4. The solvent was removed under reduced pressure and the crude material purified by column chromatography using acetone as eluent. In total 28 mg (yield 24%) of the titled compound were isolated.

Workup

  1. washThe solution was washed with a 0.4 M solution of Na2CO3
  2. customthe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe crude material purified by column chromatography

Sources & evidence

ORD record
ord-26fb6c38adc641619a54c82e94a39c75
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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