Hydrochloric Acid → HCID 68906665, compound

HRID 2099386Notes

Reaction equation

HRID 2099386 reaction equation
Cl.[Cl:2][C:3]1[CH:35]=[CH:34][C:6]([NH:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)=[C:15]([O:18][CH3:19])[CH:16]=3)[N:11]=[CH:10][N:9]=2)=[C:5]([F:36])[CH:4]=1>O1CCOCC1.C(#N)C>[ClH:2].[Cl:2][C:3]1[CH:35]=[CH:34][C:6]([NH:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[C:15]([O:18][CH3:19])[CH:16]=3)[N:11]=[CH:10][N:9]=2)=[C:5]([F:36])[CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68905043HCID 68905043, compound

Product 1

HCID 68906665HCID 68906665, compoundYield 139.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4M hydrogen chloride in dioxane (100 ml) was added to a stirred solution of tert-butyl 4-({4-[4-chloro-2-fluoroanilino]-6-methoxyquinazolin-7-yl}oxy)piperidine-1-carboxylate (7.23 g, 14.4 mmol) in acetonitrile (100 ml). The reaction mixture was heated at 70° C. for 1 hour then concentrated to ½ volume. The resulting precipitate was collected by filtration, washed with acetonitrile and dried under vacuum to give N-(4-chloro-2-fluorophenyl)-6-methoxy-7-(piperidin-4-yloxy)quinazolin-4-amine hydrochloride as a white solid (4.42 g, 76.3%); 1H NMR Spectrum: (DMSO-d6): 1.90-2.10 (m, 2H), 2.10-2.32 (m, 2H), 3.00-3.35 (m, 4H), 4.02 (s, 3H), 4.90 (m, 1H), 7.36-7.50 (m, 1H), 7.50-7.70 (m, 3H), 8.48 (s, 1H), 8.80(s, 1H), 9.30(bs, 2H), 11.90 (bs, 1H); Mass Spectrum: (M+H)+ 403.

Workup

  1. concentrationthen concentrated
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with acetonitrile
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5c39da7a62b64dceb6193af57cb0a3fe
Source dataset
uspto-grants-2009_08
Patent number
US07569577B2

Reaction notes

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