Citric Acid → HCID 15511793, compound

HRID 2217277Notes

Reaction equation

HRID 2217277 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=O)=[O:7])=[CH:4][CH:3]=1.[NH:16]1[CH2:21][CH2:20][CH:19]([N:22]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][C:23]2=[O:32])[CH2:18][CH2:17]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[K+].[Br-]>O.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@H:8]2[CH2:10][C@H:9]2[C:11]([N:16]2[CH2:17][CH2:18][CH:19]([N:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][C:23]3=[O:32])[CH2:20][CH2:21]2)=[O:13])=[O:7])=[CH:14][CH:15]=1

Participants

9

Reactant 6

HCID 311Citric AcidHCID 8471TriethylamineHCID 253877Potassium BromideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 11148817HCID 11148817, compound

Product 1

HCID 15511793HCID 15511793, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (4.452 mmol) of trans-2-(4-chlorobenzoyl)cyclopropanecarboxylic acid, 0.97 g (4.194 mmol) of 3,4-dihydro-3-(4-piperidinyl)-2(1H)-quinazolinone, 1.4 g (4.36 mmol) of TBTU, 0.455 mg (4.5 mmol) of triethylamine, and 20 mL of dimethylformamide was stirred for 5 hours at ambient temperature. The reaction mixture was freed from solvent in vacuo, diluted with 300 mL of water, and made slightly acidic with citric acid. The precipitate formed was suction filtered and carefully washed with water, then with 5 mL of tetrahydrofuran, and finally dried in a circulating air drier at a temperature of 60° C. 1.3 g (71% of theoretical) of a colorless crystalline product was obtained: m.p. 272° C.-273° C.; Rf 0.24 (MP A); IR (KBr): 1674.1 cm−1 (C═O); MS: M+=437/439 (Cl).

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washcarefully washed with water
  4. dry with materialwith 5 mL of tetrahydrofuran, and finally dried in a circulating air drier at a temperature of 60° C
  5. custom1.3 g (71% of theoretical) of a colorless crystalline product was obtained

Sources & evidence

ORD record
ord-88787c48850b4fbf949f085decc2b1c9
Source dataset
uspto-grants-2008_08
Patent number
US07407963B2

Reaction notes

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