Trifluoroacetic acid → HCID 178493872、化合物

HRID 536256ノート

反応式

HRID 536256 の反応式
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

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 178493871HCID 178493871、化合物

生成物 1

HCID 178493872HCID 178493872、化合物収率 121.5%

試薬・触媒・溶媒 2

HCID 8471Triethylamine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-478d0b13b275412a8c83c105a3c4e0e9
出典データセット
uspto-grants-2014_10
特許番号
US08859572B2

反応ノート

読み込み中…