Acetyl chloride → HCID 86703925, compound

HRID 1049928Notes

Reaction equation

HRID 1049928 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][N:13]=[C:12]3[NH2:19])[CH:5]=[C:6]([F:8])[CH:7]=1.[C:20](Cl)(=[O:22])[CH3:21]>ClCCl>[NH2:19][C:12]1[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([C:4]3[CH:3]=[C:2]([NH:1][C:20](=[O:22])[CH3:21])[CH:7]=[C:6]([F:8])[CH:5]=3)[CH:10]=2)[N:15]=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86703926HCID 86703926, compound

Product 1

HCID 86703925HCID 86703925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 4 mL screw-cap vial was added 6-(3-amino-5-fluoro-phenyl)quinazolin-4-amine, 25 mg; 0.10 mmol) followed by DCM (0.5 mL), TEA (2 equiv., 0.20 mmol, 0.0277 mL), and acetyl chloride (2 equiv., 0.20 mmol, 15.43 mg). The reaction was capped and shaken at room temperature for 2 h. Reaction was then diluted with 2 mL dichloromethane, and washed with water. Resultant precipitate was collected by filtration, then purified by reverse phase HPLC. Purification recovered 6 mg of desired product. 1H NMR (400 MHz, DMSO) δ 10.35-10.24 (s, 1H), 8.61-8.49 (d, J=1.7 Hz, 1H), 8.43-8.36 (s, 1H), 8.05-7.97 (dd, J=8.7, 1.8 Hz, 1H), 7.98-7.82 (bs, 1H), 7.77-7.73 (d, J=8.7 Hz, 1H), 7.71-7.67 (s, 1H), 7.65-7.56 (d, J=11.2 Hz, 1H), 7.42-7.30 (d, J=10.0 Hz, 1H), 2.11-2.08 (s, 3H). LCMS M/Z (M+H) 297.

Workup

  1. customTo a 4 mL screw-cap vial
  2. customThe reaction was capped
  3. customReaction
  4. washwashed with water
  5. filtrationResultant precipitate was collected by filtration
  6. custompurified by reverse phase HPLC
  7. customPurification
  8. customrecovered 6 mg of desired product

Sources & evidence

ORD record
ord-cc81362e0e7d40b8966b2bcc8320bd95
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

Loading…