Hydrochloric Acid → HCID 135433484, compound

HRID 2183576Notes

Reaction equation

HRID 2183576 reaction equation
[SH:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:14][C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(N(CC)CC)C.Cl>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:18][C:16](=[O:17])[C:15](=[O:21])[CH2:14][S:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 66144Ethyl bromopyruvateHCID 178518761HCID 178518761, compound

Product 1

HCID 135433484HCID 135433484, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

An homogeneous solution of 2-mercapto-3H-quinazolin-4-one (1.30 g, 7.17 mmol) and ethyl bromopyruvate (1 mL, 7.17 mmol, 90% purity) in DMF (30 mL) was stirred at room temperature for 6 h. Triethylamine (5 mL) was added to the solution and the mixture was stirred at room temperature for 36 h. The mixture was acidified to pH 1-2 with concentrated hydrochloric acid and then rotary evaporated to dryness. The residue was separated by column chromatography eluted with EtOAc giving the title compound as yellow solid (0.231 g, yield 11.0%). 1H NMR (DMSO-d6, 300.16 MHz) δ (ppm): 8.05 (dd, J=7.9 & 1.4 Hz, 1H), 8.01 (s, 1H), 7.81 (td, J=8.3 & 1.5 Hz, 1H), 7.53 (d, J=8.2 Hz, 1H), 7.46 (td, J=7.5 & 1.4 Hz, 1H), 4.21 (q, J=7.1 Hz, 2H), 3.82 (d, J=12.2 Hz, 1H), 3.46 (d, J=12.2 Hz, 1H) and 1.18 (t, J=7.1 Hz, 3H). 13C NMR (DMSO-d6, 75.48 MHz) δ (ppm): 168.06, 159.54, 159.26, 149.07, 135.98, 126.85, 126.74, 126.36, 119.09, 91.33, 62.79, 37.92 and 14.31. MS (ESI) m/z: 293 (M++H, 100).

Workup

  1. customrotary evaporated to dryness
  2. customThe residue was separated by column chromatography

Sources & evidence

ORD record
ord-537948fbe9824903a23022653aec6110
Source dataset
uspto-grants-2005_05
Patent number
US06900218B2

Reaction notes

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