HCID 57856118, compound → HCID 57856195, compound

HRID 2401950Notes

Reaction equation

HRID 2401950 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13](Cl)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH:16]1[C:25]2[C:24]3[CH:26]=[CH:27][O:28][C:23]=3[CH2:22][CH2:21][C:20]=2[N:19]=[C:18]([NH2:29])[N:17]=1>N1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:29][C:18]4[N:17]=[CH:16][C:25]5[CH2:24][CH2:26][C:27]6[O:28][CH:23]=[CH:22][C:21]=6[C:20]=5[N:19]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 57856118HCID 57856118, compoundHCID 591291541-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

Product 1

HCID 57856195HCID 57856195, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

To 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (45 mg, 0.2 mmol) in pyridine (2 mL) was added 5,6-dihydrofuro[3,2-f]quinazolin-3-amine (37 mg, 0.2 mmol) and the reaction mixture was stirred at 115° C. for 15 hours. The solvent was evaporated to dryness and the residue redissolved in DMF, filtered and purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoracetic acid to yield the pure product. ESI-MS m/z calc. 375.4, found 375.1 (M+1)+. Retention time 2.61 minutes.

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionthe residue redissolved in DMF
  3. filtrationfiltered
  4. custompurified by reverse-phase preparative liquid chromatography
  5. customto yield the pure product

Sources & evidence

ORD record
ord-751c8c36fac547a6a5bd2dd9663737f2
Source dataset
uspto-grants-2014_08
Patent number
US08796312B2

Reaction notes

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