Methylamine → HCID 86715532, compound

HRID 2284615Notes

Reaction equation

HRID 2284615 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[C:13]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Cl:25])[CH:19]=4)=[N:14][CH:15]=[CH:16][CH:17]=3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:26][NH2:27]>C1COCC1.CC(O)C>[Cl:25][C:20]1[CH:19]=[C:18]([C:13]2[C:12]([C:9]3[CH:10]=[C:11]4[C:6](=[CH:7][CH:8]=3)[N:5]=[CH:4][N:3]=[C:2]4[NH:27][CH3:26])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:23]=[CH:22][C:21]=1[F:24]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 86715533HCID 86715533, compound

Product 1

HCID 86715532HCID 86715532, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-6-(2-(3-chloro-4-fluorophenyl)pyridin-3-yl)quinazoline (75 mg), 2M MeNH2 in THF (2 mL) and i-PrOH (3 mL) were heated and stirred in a screw capped vial for 12 h at 65° C. The heterogeneous reaction mixture was cooled and filtered. The solid on the funnel was washed with water and dried to obtain 6-(2-(3-chloro-4-fluorophenyl)pyridin-3-yl)-N-methylquinazolin-4-amine (53 mg) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 8.72 (dd, J=4.7, 1.7 Hz, 1H), 8.47 (s, 1H), 8.31 (q, J=4.7 Hz, 1H), 8.25 (d, J=1.9 Hz, 1H), 7.95 (dd, J=7.8, 1.7 Hz, 1H), 7.61-7.50 (m, 3H), 7.36 (dd, J=8.6, 1.9 Hz, 1H), 7.24 (t, J=8.9 Hz, 1H), 7.13 (ddd, J=8.6, 4.8, 2.2 Hz, 1H), 2.98 (d, J=4.4 Hz, 3H). 19F NMR (282 MHz, DMSO-d6): δ −117.17 (td, J=8.6, 5.1 Hz). LCMS: rt 4.68 min (A), purity 99%, MS (m/e) 365 MH+.

Workup

  1. customcapped vial for 12 h at 65° C
  2. temperatureThe heterogeneous reaction mixture was cooled
  3. filtrationfiltered
  4. washThe solid on the funnel was washed with water
  5. customdried

Sources & evidence

ORD record
ord-7ca084375b974184b7d4312a8117c29b
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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