Methanol → HCID 178486727, compound

HRID 890977Notes

Reaction equation

HRID 890977 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][NH:7][C:8]([NH:32][C:33]1[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:40])=[N:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)=[O:4].O.[OH-].[Li+].C1COCC1.CO>O>[C:3]([CH2:5][CH2:6][NH:7][C:8]([NH:32][C:33]1[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:40])=[N:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)([OH:4])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 178500816HCID 178500816, compound

Product 1

HCID 178486727HCID 178486727, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(2-methoxycarbonylethyl)-N′-(2,6-dimethylphenyl)-N″-[6-methoxy-7-(3-morpholinopropoxy)quinazolin-4-yl]guanidine (0.038 g), lithium hydroxide monohydrate (0.0063 g), THF (1 ml), methanol (0.5 ml) and water (0.5 ml) was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was partitioned between water and methylene chloride. The aqueous layer was acidified by the addition of glacial acetic acid and evaporated. The resultant residue was extracted with methylene chloride. The organic extract was filtered and evaporated. There was thus obtained the title compound (0.034 g); NMR Spectrum: (CDCl3) 2.15 (m, 2H), 2.28 (s, 6H), 2.58 (s, 3H), 2.6–2.73 (m, 7H), 3.73 (t, 4H), 3.83 (s, 2H), 4.0 (s, 4H), 4.2 (t, 2H), 7.14 (s, 3H), 7.2 (s, 1H), 7.87 (s, 1H), 8.51 (s, 1H), 12.5 (s, 1H); Mass Spectrum: M+H+ 538.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between water and methylene chloride
  3. additionThe aqueous layer was acidified by the addition of glacial acetic acid
  4. customevaporated
  5. extractionThe resultant residue was extracted with methylene chloride
  6. extractionThe organic extract
  7. filtrationwas filtered
  8. customevaporated

Sources & evidence

ORD record
ord-36510be6441d4bec9774cc740e48de48
Source dataset
uspto-grants-2006_02
Patent number
US07001904B1

Reaction notes

Loading…