Trifluoroacetic acid → HCID 178493872, 화합물

HRID 536256노트

반응식

HRID 536256 반응식
C(OC(=O)[NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14](=[O:44])[NH:15][C:16]2[N:25]3[CH2:26][CH2:27][N:28]=[C:24]3[C:23]3[CH:22]=[CH:21][C:20]([O:29][CH2:30][CH2:31][CH2:32][S:33]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)(=[O:35])=[O:34])=[C:19]([O:42][CH3:43])[C:18]=3[N:17]=2)=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCN(CC)CC>[NH2:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([NH:15][C:16]2[N:25]3[CH2:26][CH2:27][N:28]=[C:24]3[C:23]3[CH:22]=[CH:21][C:20]([O:29][CH2:30][CH2:31][CH2:32][S:33]([N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)(=[O:35])=[O:34])=[C:19]([O:42][CH3:43])[C:18]=3[N:17]=2)=[O:44])=[CH:10][N:9]=1

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 178493871HCID 178493871, 화합물

생성물 1

HCID 178493872HCID 178493872, 화합물수율 121.5%

시약·촉매·용매 2

HCID 8471Triethylamine촉매HCID 6344Dichloromethane용매

실험 절차

tert-Butyl[5-({7-methoxy-8-[3-(morpholin-4-ylsulfonyl)propoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl}carbamoyl)pyrimidin-2-yl]carbamate (Step 1, 150 mg 0.26 mmol) was dissolved in CH2Cl2 (15 mL) and TFA (0.16 mL, 2.1 mmol) was added dropwise. The mixture was stirred at rt over 2 d, after which 5 drops of Et3N were added causing a solid to precipitate. The mixture was stirred overnight, then the solvents removed under reduced pressure. The resulting residue was triturated in EtOAc (15 mL), collected by vacuum filtration and washed further with EtOAc (10 mL). This solid was then triturated in water (5 mL) collected by vacuum filtration and washed further with water (10 mL). High vacuum drying gave the title compound (172 mg, 92%): HPLC MS RT=0.87 min, MH+=545.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.21-2.26 (2H, m), 3.15-3.18 (4H, m), 3.24-3.29 (2H, m), 3.61-3.65 (4H, m), 3.99 (3H, s), 4.18-4.25 (2H, m), 4.37 (2H, t), 4.48-4.55 (2H, m), 7.44 (1H, d), 8.02 (1H, d), 9.06 (2H, s).

후처리

  1. customto precipitate
  2. stirringThe mixture was stirred overnight
  3. customthe solvents removed under reduced pressure
  4. customThe resulting residue was triturated in EtOAc (15 mL)
  5. filtrationcollected by vacuum filtration
  6. washwashed further with EtOAc (10 mL)
  7. customThis solid was then triturated in water (5 mL)
  8. filtrationcollected by vacuum filtration
  9. washwashed further with water (10 mL)
  10. customHigh vacuum drying

출처 및 근거

ORD 기록
ord-478d0b13b275412a8c83c105a3c4e0e9
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859572B2

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