Water → HCID 178486910, compound

HRID 1295739Notes

Reaction equation

HRID 1295739 reaction equation
[CH3:1][S:2]([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[CH2:9][NH:10][CH3:11])=[O:3].Cl[C:16]1[NH:17][C:18]2[C:23]([C:24](=[O:26])[N:25]=1)=[C:22]([CH3:27])[C:21]([O:28][CH3:29])=[C:20]([O:30][CH3:31])[CH:19]=2.CCN(CC)CC.O>CS(C)=O>[CH3:1][S:2]([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[CH2:9][N:10]([CH3:11])[C:16]1[NH:17][C:18]2[C:23]([C:24](=[O:26])[N:25]=1)=[C:22]([CH3:27])[C:21]([O:28][CH3:29])=[C:20]([O:30][CH3:31])[CH:19]=2)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 69508634HCID 69508634, compoundHCID 178486897HCID 178486897, compound

Product 1

HCID 178486910HCID 178486910, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Compound from step 4 (213 mg, 1.00 mmol) and 2-chloro-6,7-dimethoxy-5-methyl-1H-quinazolin-4-one (254 mg, 1.00 mmol) were dissolved in dry DMSO. Et3N (0.14 mL, 1.00 mmol) was added, and the mixture was heated to 120° C. overnight. Upon cooling, the mixture was poured into water and extracted with diethyl ether. The ethereal extracts were dried over Na2SO4 and concentrated in vacuo. The residue was recrystallized from MeOH to give 54 mg (12.53%) of the above Example F-2 as a white crystalline powder. mp 191.0–193.5° C.; 1H NMR (DMSO-d6, 2.49) δ 2.59 (s, 3 H), 2.60 (s, 3 H), 3.03 (s, 3 H), 3.62 (s, 3 H), 3.84 (s, 3 H), 4.79 (s, 2 H), 5.02 (d, 1 H, J=10.6), 5.22 (d, 1 H, J=10.6), 6.64 (s, 1 H), 6.90 (d, 1 H, J=7.6), 7.01 (m, 2 H), 7.30 (t, 1 H, J=7.9); 13C NMR (DMSO-d6, 39.50) δ 13.90, 34.66, 35.59, 51.90, 55.93, 60.23, 84.92, 104.81, 108.46, 114.18, 115.02, 121.22, 130.13, 131.94, 140.10, 142.90, 150.63, 150.97, 157.71, 157.97, 163.67; MS (ES+) m/z 432 (M+H); Anal. (C21H25N3O5S)C: calcd, 58.45; found, 58.32; H: calcd, 5.84; found, 5.74; N: calcd, 9.74; found, 9.77.

Workup

  1. temperatureUpon cooling
  2. extractionextracted with diethyl ether
  3. dry with materialThe ethereal extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from MeOH
  6. customto give 54 mg (12.53%) of the above Example F-2 as a white crystalline powder

Sources & evidence

ORD record
ord-73e390abf8a445829d0ce5f97a5525b4
Source dataset
uspto-grants-2007_07
Patent number
US07244738B2

Reaction notes

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