Trifluoroacetic acid → {5-[5-(2-Morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl]-pyridin-2-yl}-(4-trifluoromethyl-benzyl)-amine

HRID 2387272노트

반응식

HRID 2387272 반응식
C(OC(=O)[N:7]([C:19]1[CH:24]=[CH:23][C:22]([CH:25](O)[C:26]2[C:34]3[C:29](=[N:30][CH:31]=[C:32]([O:35][CH2:36][CH2:37][N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)[CH:33]=3)[NH:28][CH:27]=2)=[CH:21][N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[N:38]1([CH2:37][CH2:36][O:35][C:32]2[CH:33]=[C:34]3[C:26]([CH2:25][C:22]4[CH:23]=[CH:24][C:19]([NH:7][CH2:8][C:9]5[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=5)=[N:20][CH:21]=4)=[CH:27][NH:28][C:29]3=[N:30][CH:31]=2)[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59593292(5-(Hydroxy-[5-(2-morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methyl}-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester

생성물 1

HCID 59593302{5-[5-(2-Morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl]-pyridin-2-yl}-(4-trifluoromethyl-benzyl)-amine수율 11.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of (5-{Hydroxy-[5-(2-morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methyl}-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (24, 0.2 g, 0.3 mmol), triethylsilane (4 mL, 0.02 mol), and trifluoroacetic acid (2 mL, 0.02 mol) in acetonitrile (30 mL) was refluxed for 2 hours. After removal of solvent, the residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate, brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with methanol in dichloromethane to provide the compound as a light yellow solid (25, 17 mg, 10%). MS (ESI) [M+H+]+=512.42.

후처리

  1. temperaturewas refluxed for 2 hours
  2. customAfter removal of solvent
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of solvent
  7. customthe residue was purified by silica gel column chromatography
  8. washeluting with methanol in dichloromethane

출처 및 근거

ORD 기록
ord-7cfc7156ac534e05b50093873ef11614
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268858B2

반응 노트

불러오는 중…