Hydrochloric Acid → HCID 68904833, compound

HRID 2099381Notes

Reaction equation

HRID 2099381 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.[Cl:29][C:30]1[CH:31]=[C:32]([CH:34]=[CH:35][C:36]=1[F:37])[NH2:33]>O1CCOCC1.C(#N)C>[ClH:2].[Cl:29][C:30]1[CH:31]=[C:32]([NH:33][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH:16]4[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]4)=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[CH:5][N:4]=2)[CH:34]=[CH:35][C:36]=1[F:37]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 97083-Chloro-4-fluoroanilineHCID 596829067-{[1-(Tert-butoxycarbonyl)-piperidin-4-yl]oxy}-4-chloro-6-methoxyquinazoline

Product 1

HCID 68904833HCID 68904833, compoundYield 153.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

4.0M HCl in Dioxane (1 ml) was added to a suspension of tert-butyl 4-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]piperidine-1-carboxylate (331 mg, 0.84 mmol) and 3-chloro-4-fluoroaniline (134.5 mg) in acetonitrile (10 ml). The reaction mixture was stirred and heated at 70° C. for 4 hours. The resulting precipitate was filtered hot, washed with acetonitrile and dried under vacuum to give N-(3-chloro-4-fluorophenyl)-6-methoxy-7-(piperidin-4-yloxy)quinazolin-4-amine hydrochloride (566 mg); Mass Spectrum: (M+H)+ 403.

Workup

  1. filtrationThe resulting precipitate was filtered hot
  2. washwashed with acetonitrile
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d725852bc2cd4c4cb1590e9fca7f7be4
Source dataset
uspto-grants-2009_08
Patent number
US07569577B2

Reaction notes

Loading…