Dimethylamine → HCID 10392843, compound

HRID 1948912Notes

Reaction equation

HRID 1948912 reaction equation
[Cl:1][C:2]1[C:3]([F:35])=[C:4]([CH:32]=[CH:33][CH:34]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:30][CH3:31])=[C:13]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([S:23]([CH2:26][CH2:27][CH2:28]Cl)(=[O:25])=[O:24])[CH2:19][CH2:18]3)[CH:14]=2)[N:9]=[CH:8][N:7]=1.[I-].[Na+].[CH3:38][NH:39][CH3:40]>>[Cl:1][C:2]1[C:3]([F:35])=[C:4]([CH:32]=[CH:33][CH:34]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:30][CH3:31])=[C:13]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([S:23]([CH2:26][CH2:27][CH2:28][N:39]([CH3:40])[CH3:38])(=[O:24])=[O:25])[CH2:19][CH2:18]3)[CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 68522468HCID 68522468, compound

Product 1

HCID 10392843HCID 10392843, compound

Procedure

A suspension of 4-(3-chloro-2-fluoroanilino)-6-{1-[3-chloropropylsulfonyl]piperidin-4-yloxy}-7-methoxyquinazoline (0.15 g) and sodium iodide (0.03 g) in an ethanolic solution of dimethylamine (33%) (15 ml) was stirred at ambient temperature for 16 hours. The reaction mixture was adsorbed onto silica and purified by column chromatography on silica eluting with increasingly polar mixtures of methylene chloride/methanol (saturated with ammonia) (100/0 to 88/12). The fractions containing the title product were combined and evaporated under vacuum to give the title product (0.105 g); 1H NMR Spectrum: (DMSO d6) 1.75-1.87 (m, 4H), 2.0-2.11 (m, 2H), 2.12 (s, 6H), 2.30 (t, 2H), 3.05-3.14 (m, 2H), 3.17-3.29 (m, 2H), 3.40-3.50 (m, 2H), 3.93 (s, 3H), 4.69 (m, 1H), 7.22 (s, 1H), 7.28 (t, 1H), 7.44-7.55 (m, 2H), 7.86 (s, 1H), 8.37 (s, 1H), 9.53 (s, 1H); Mass Spectrum: (M+H)+ 552

Workup

  1. custompurified by column chromatography on silica eluting
  2. temperaturewith increasingly polar mixtures of methylene chloride/methanol (saturated with ammonia) (100/0 to 88/12)
  3. additionThe fractions containing the title product
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-a086c14d57a14030bd61a2f4fea24891
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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