Trifluoroacetic acid → 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(1-methyl-3-(piperidin-4-yl)-1H-1,2,4-triazol-5-yl)pyrazin-2-amine

HRID 1749679노트

반응식

HRID 1749679 반응식
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:17]2[N:21]([CH3:22])[N:20]=[C:19]([CH:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)[N:18]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:11][N:12]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:13]([C:10]1[O:9][C:8]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:17]3[N:21]([CH3:22])[N:20]=[C:19]([CH:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]4)[N:18]=3)[N:6]=2)=[N:12][N:11]=1)([CH3:16])([CH3:14])[CH3:15]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86727657tert-butyl 4-(5-(5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-1-methyl-1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate

생성물 1

HCID 867276583-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(1-methyl-3-(piperidin-4-yl)-1H-1,2,4-triazol-5-yl)pyrazin-2-amine수율 103%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl 4-(5-(5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-1-methyl-1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate (36.81 g, 76.12 mmol) was added to a solution of 2,2,2-trifluoroacetic acid (100 mL, 1305.87 mmol) in DCM (100 mL). The mixture was stirred for 3 hours at room temperature. The mixture was concentrated under reduced pressure. The residue was dissolved in DCM (1.5 L) and added to vigorously stirred concentrated ammonia (150 mL) in water (400 mL). The aqueous was washed with DCM (400 mL) and the combined organic solutions were dried with magnesium sulfate, filtered and concentrated to dryness to afford 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(1-methyl-3-(piperidin-4-yl)-1H-1,2,4-triazol-5-yl)pyrazin-2-amine (30.0 g, 103%) as a yellow solid:

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DCM (1.5 L)
  3. additionadded
  4. stirringto vigorously stirred concentrated ammonia (150 mL) in water (400 mL)
  5. washThe aqueous was washed with DCM (400 mL)
  6. dry with materialthe combined organic solutions were dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-97e5fce3c26a4aebad79a7821304fcd6
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156831B2

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