Water → HCID 178486910, 화합물

HRID 1295739노트

반응식

HRID 1295739 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 69508634HCID 69508634, 화합물HCID 178486897HCID 178486897, 화합물

생성물 1

HCID 178486910HCID 178486910, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-73e390abf8a445829d0ce5f97a5525b4
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244738B2

반응 노트

불러오는 중…