Triphenylphosphine → 2-(4-(4-((2-Methylpyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)-5-(trifluoromethyl)pyrimidine

HRID 80664

반응식

HRID 80664 반응식
[NH:1]1[C:5]([CH2:6][O:7][C:8]2[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][N:3]=[N:2]1.[F:15][C:16]([F:31])([F:30])[C:17]1[CH:18]=[N:19][C:20]([N:23]2[CH2:28][CH2:27][CH:26](O)[CH2:25][CH2:24]2)=[N:21][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C1COCC1>[CH3:14][C:9]1[C:8]([O:7][CH2:6][C:5]2[CH:4]=[N:3][N:2]([CH:26]3[CH2:27][CH2:28][N:23]([C:20]4[N:19]=[CH:18][C:17]([C:16]([F:15])([F:30])[F:31])=[CH:22][N:21]=4)[CH2:24][CH2:25]3)[N:1]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 577084291-(5-(Trifluoromethyl)pyrimidin-2-yl)piperidin-4-ol2회HCID 178432688HCID 178432688, 화합물

생성물 1

HCID 577083962-(4-(4-((2-Methylpyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)-5-(trifluoromethyl)pyrimidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-((1H-1,2,3-triazol-5-yl)methoxy)-2-methylpyridine (0.20 g, 1.05 mmol), in THF (2 mL) at 0° C., was added 1-(5-(trifluoromethyl)pyrimidin-2-yl)piperidin-4-ol (0.391 g, 1.58 mmol) (Intermediate 20), polymer bound triphenylphosphine (0.527 g, 1.58 mmol), and di-tert-butylazodicarboxylate (0.363, 1.58 mmol). The reaction was allowed to warm to room temperature overnight and was then filtered through a pad of celite washing with THF. The solution was concentrated in vacuo and purified by flash column chromatography on silica gel eluting with 0-60% ethyl acetate in hexane to afford the desired product. 1H NMR (DMSO-d6): δ 8.71 (2H, s), 8.00 (1H, dd), 7.89 (1H, s), 7.47 (1H, dd), 7.19 (1H, dd), 5.18 (2H, s), 4.90 (1H, m), 4.68 (2H, s), 3.31 (2H, m), 2.31 (3H, s), 2.19 (2H, m), 1.92 (2H, m).

후처리

  1. filtrationwas then filtered through a pad of celite
  2. washwashing with THF
  3. concentrationThe solution was concentrated in vacuo
  4. custompurified by flash column chromatography on silica gel eluting with 0-60% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-97bcc7f977e048a9a03526830386bdf4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846675B2

연결된 노트

불러오는 중…