Acetic Acid → HCID 11974119, compound

HRID 1373322Notes

Reaction equation

HRID 1373322 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[C:21]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:40][CH:41]([CH3:43])[CH3:42])=[CH:30][C:31]=3[O:33][CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[N:26]=[CH:25][N:24]=2)=[C:20]2[O:44][CH2:45][O:46][C:19]2=[CH:18][CH:17]=1.C=O.C(O)(=O)C>CO.C(Cl)Cl>[Cl:15][C:16]1[C:21]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:40][CH:41]([CH3:42])[CH3:43])=[CH:30][C:31]=3[O:33][CH:34]3[CH2:35][CH2:36][N:37]([CH3:1])[CH2:38][CH2:39]3)[N:26]=[CH:25][N:24]=2)=[C:20]2[O:44][CH2:45][O:46][C:19]2=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11974719HCID 11974719, compound

Product 1

HCID 11974119HCID 11974119, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.087 g) was added portionwise to a stirred mixture of 4-(6-chloro-2,3-methylenedioxyanilino)-7-isopropoxy-5-piperidin-4-yloxyquinazoline (0.125 g), aqueous formaldehyde (13N, 0.042 ml), acetic acid (0.019 ml), methylene chloride (5 ml) and methanol (2 ml) and the resultant mixture was heated to reflux for 3 minutes. The mixture was evaporated and the residue was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution. The organic layer was washed with brine, dried over magnesium sulphate and evaporated to give the title compound (0.11 g); NMR Spectrum: (CDCl3) 1.42 (d, 6H), 1.95–2.1 (m, 2H), 2.15–2.25 (m, 2H), 2.3 (s, 3H), 2.3–2.4 (m, 2H), 2.7–2.8 (m, 2H), 4.6 (m, 1H), 4.72 (m, 1H), 6.05 (s, 2H), 6.5 (d, 1H), 6.75 (d, 1H), 6.82 (d, 1H), 6.99 (d, 1H), 8.52 (s, 1H), 9.3 (s, 1H); Mass Spectrum: M+H+ 471 and 473.

Workup

  1. temperatureto reflux for 3 minutes
  2. customThe mixture was evaporated
  3. customthe residue was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-d987436801ad4e08965f546aa721842e
Source dataset
uspto-grants-2007_01
Patent number
US07160891B2

Reaction notes

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