Trifluoroacetic acid → HCID 86695247, 화합물

HRID 1504083노트

반응식

HRID 1504083 반응식
[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

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86695246HCID 86695246, 화합물

생성물 1

HCID 86695247HCID 86695247, 화합물

시약·촉매·용매 1

HCID 21908982Water methylene chloride용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-17ad39b5cb9f4830b4bd44eb37f41500
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212190B2

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