Diisopropylethylamine → N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide

HRID 25162

반응식

HRID 25162 반응식
Cl.[Br:2][C:3]1[N:7]2[CH:8]=[C:9]([C:12]([OH:14])=O)[N:10]=[CH:11][C:6]2=[CH:5][CH:4]=1.[C:15]1([NH2:26])[C:20](F)=[C:19](F)[C:18](F)=[C:17](N)C=1F.Cl.Cl.[CH3:29][CH2:30][N:31](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C1COCC1>[N:26]12[CH2:17][CH2:18][CH:19]([CH2:20][CH2:15]1)[C@@H:30]([NH:31][C:12]([C:9]1[N:10]=[CH:11][C:6]3[N:7]([C:3]([Br:2])=[CH:4][CH:5]=3)[CH:8]=1)=[O:14])[CH2:29]2

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69713212588720-63-2

생성물 1

HCID 10247203N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 6-bromopyrrolo[1,2-a]pyrazine-3-carboxylic acid hydrochloride (1.67 mmol), (R)-3-aminoquinulidine dihydrochloride (0.34 g, 1.67 mmol), DIEA (1.5 mL, 8.35 mmol) in DMF (20 mL) and THF (10 mL) is added HATU (0.64 g, 1.67 mmol). The resulting suspension is stirred for 16 h at which time it is concentrated to dryness under reduced pressure. The resulting material is absorbed to silica gel and purified with silica gel chromatography (9% MeOH/1%NH3OH/CH2Cl2 as the eluent) salted with fumeric acid, and crystallized from EtOH/acetone/Et2O to give an off white spheres. Yield 45%. HRMS (FAB) calcd. for C15H17BrN4O+H 349.0664, found 349.0647.

후처리

  1. concentrationis concentrated to dryness under reduced pressure
  2. customThe resulting material is absorbed to silica gel
  3. custompurified with silica gel chromatography (9% MeOH/1%NH3OH/CH2Cl2 as the eluent)
  4. customcrystallized from EtOH/acetone/Et2O
  5. customto give an off white spheres

출처 및 근거

ORD 기록
ord-719641f08ec94b06a39361fb8608fa61
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858613B2

연결된 노트

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