Hydrochloric Acid → HCID 68521486, compound

HRID 1948960Notes

Reaction equation

HRID 1948960 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:27][CH3:28])=[C:10]([O:13][C@H:14]3[CH2:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]3)[CH:11]=2)[N:6]=[CH:5][N:4]=1.[Cl:29][C:30]1[C:31]([F:37])=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH2:33]>C(#N)C>[ClH:2].[Cl:29][C:30]1[C:31]([F:37])=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH:33][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:27][CH3:28])=[C:10]([O:13][C@H:14]3[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]3)[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 750143-Chloro-2-fluoroanilineHCID 86624373HCID 86624373, compound

Product 1

HCID 68521486HCID 68521486, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

HCl (1.0 ml, 4M solution in dioxane) was added to 4-chloro-7-methoxy-6-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yloxy]quinazoline (0.786 g) and 3-chloro-2-fluoroaniline (0.304 g) dissolved in acetonitrile (25 ml). The mixture was heated to 60° C. for 2 hours, cooled and the precipitate collected to give 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-[(3S)-piperidin-3-yloxy]quinazoline hydrochloride as a white solid (0.577 g, 66%); 1H NMR Spectrum: (DMSOd6) 1.70-1.95 (m, 2H), 1.95-2.10 (m, 1H); 2.10-2.25 (m, 1H), 2.95-3.10 (m, 1H), 3.10-3.30 (m, 2H), 3.45-3.65 (m, 1H); 4.03 (s, 3H); 4.95-5.10 (m, 1H); 7.30-7.45 (m, 1H); 7.45-7.60 (m, 2H); 7.60-7.73 (m, 1H), 8.85 (s, 1H); 8.90 (s, 1H); 9.15 (bs, 2H); 12.3 (bs, 1H); Mass Spectrum: (M+H): 403.

Workup

  1. temperaturecooled
  2. customthe precipitate collected

Sources & evidence

ORD record
ord-b6de745de2614a7087c58c0f0e1f0717
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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