Trifluoroacetic acid → HCID 86695247、化合物

HRID 1504083ノート

反応式

HRID 1504083 の反応式
[N:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[C:15]4[CH:22]=[C:21]([CH2:23][CH2:24][NH:25][C:26](=O)OC(C)(C)C)[S:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>C(Cl)Cl.O>[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[N:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[C:15]4[C:22]5[CH2:26][NH:25][CH2:24][CH2:23][C:21]=5[S:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH2:9][CH2:8]2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86695246HCID 86695246、化合物

生成物 1

HCID 86695247HCID 86695247、化合物

試薬・触媒・溶媒 1

HCID 21908982Water methylene chloride溶媒

実験手順

To a solution of tert-butyl N-[2-(4-[[4-(morpholin-4-yl)cyclohexyl]oxy]thieno[2,3-d]pyrimidin-6-yl)ethyl]carbamate (150 mg, 0.32 mmol, 1.00 equiv) in DCM/H2O (10/0.5 mL) was added trifluoroacetic acid (0.8 mL) at 0° C. and stirred overnight at room temperature. After concentration under vacuum, the residue was dissolved in DCE (30 mL) and paraformaldehyde (180 mg) and trifluoroacetic acid (1 mL) were added. The resulting solution was stirred overnight at 45° C. under nitrogen. After concentration under vacuum, the residue was purified by preparative HPLC under the following conditions: Column: XBridge Shield RP18 OBD, 5 μm, 19*150 mm; mobile phase: water (with 0.5% TFA) and CH3CN (0% CH3CN up to 21% in 12 min, up to 95% in 2 min, down to 0% in 2 min); flow rate: 20 mL/min; UV detection at 254/220 nm. After concentration under vacuum, the desired 3-[[4-(morpholin-4-yl)cyclohexyl]oxy]-8-thia-4,6,12-triazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraene trifluoroacetate (100 mg, crude) was obtained as a light yellow solid. MS (ES): m/z 375 (M+H)+.

後処理

  1. concentrationAfter concentration under vacuum
  2. dissolutionthe residue was dissolved in DCE (30 mL)
  3. additionparaformaldehyde (180 mg) and trifluoroacetic acid (1 mL) were added
  4. stirringThe resulting solution was stirred overnight at 45° C. under nitrogen
  5. concentrationAfter concentration under vacuum
  6. customthe residue was purified by preparative HPLC under the following conditions
  7. waitmobile phase: water (with 0.5% TFA) and CH3CN (0% CH3CN up to 21% in 12 min
  8. waitup to 95% in 2 min
  9. waitdown to 0% in 2 min)
  10. concentrationAfter concentration under vacuum

出典と根拠

ORDレコード
ord-17ad39b5cb9f4830b4bd44eb37f41500
出典データセット
uspto-grants-2015_12
特許番号
US09212190B2

反応ノート

読み込み中…