Hydrochloric Acid → {2,4-dioxo-3-[4-(phenethylcarbamoyl-methyl)-phenyl]-3,4-dihydro-2H-quinazolin-1-yl}-acetic acid tert-butyl ester

HRID 472746Notes

Reaction equation

HRID 472746 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:29])=O)=[CH:22][CH:21]=2)[C:10]1=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:7])[CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27](=[O:29])[NH:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:22][CH:21]=2)[C:10]1=[O:30])([CH3:3])([CH3:2])[CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1001PhenethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68589939[4-(1-tert-butoxycarbonylmethyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acetic acid2×

Product 1

HCID 68593254{2,4-dioxo-3-[4-(phenethylcarbamoyl-methyl)-phenyl]-3,4-dihydro-2H-quinazolin-1-yl}-acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of [4-(1-tert-butoxycarbonylmethyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acetic acid (Intermediate F) (932 mg, 2.27 mmol), 2-(aminoethyl)benzene (1.2 eq, 344 mg, 2.72 mmol) and HATU (1.2 eq, 1.035 g. 2.72 mmol) in DCM (8 ml) is treated with DIPEA (2 eq, 711 μL, 4.54 mmol). The reaction mixture is stirred at RT for 48 hours. The mixture is diluted with distilled water (5 ml) followed by 0.1 M HCl (5 ml) and extracted with EtOAc (2×15 ml). The combined organic portions are washed with aqueous saturated aqueous NaHCO3, dried (MgSO4) and concentrated in vacuo.

Workup

  1. extractionextracted with EtOAc (2×15 ml)
  2. washThe combined organic portions are washed with aqueous saturated aqueous NaHCO3
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0de42422e264048a931d14bff3540a6
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

Loading…