Ethyl formate → HCID 59164533, compound

HRID 906568Notes

Reaction equation

HRID 906568 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[NH:9][C:8](=[O:17])[N:7]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:6]2=[O:23].[CH:24](OCC)=[O:25]>C1COCC1>[CH:24]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[C:13]([F:15])([F:16])[F:14])[NH:9][C:8](=[O:17])[N:7]([NH:18][S:19]([CH3:22])(=[O:20])=[O:21])[C:6]2=[O:23])=[O:25]

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 59164454HCID 59164454, compound

Product 1

HCID 59164533HCID 59164533, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of N-(6-aminomethyl-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (400 mg, 1.14 mmol) in ethyl formate (27.4 mL, 340.7 mmol) and THF (25 mL) was stirred at 60° C. for 16 h. Subsequently the solvent was evaporated and the residue dried in vacuo for 2 h. The crude product was purified by flash-master chromatography (DCM 100-90/MeOH 0-10, %-gradients) to yield N-(6-formylaminomethyl-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (316 mg, 0.831 mmol, 73%) as a light-yellow solid. 1H-NMR (DMSO-d6, 400 MHz) 3.17 ppm (s, 3H, SO2—CH); LC-MS rt=2.32 min; MS: m/z 380.9 [M+H]+ Column: SunFireC18, 4.6*50 mn, 3.5 um; Positive MS Water/Acetonitrile 95:5 to 5:95 in 5 min, Flow: 1.5 mL/min

Workup

  1. customSubsequently the solvent was evaporated
  2. customthe residue dried in vacuo for 2 h
  3. customThe crude product was purified by flash-master chromatography (DCM 100-90/MeOH 0-10, %-gradients)

Sources & evidence

ORD record
ord-635208062d604b50bd24d7f4ae83790d
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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