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Acetic Acid → HCID 11974119, compound

HRID 1826311
Notes
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Reaction equation

HRID 1826311 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent
HCID 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-da5a795beb7c4593b514a328310465e8
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07049438B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes