Dimethylformamide → (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-(tert-butoxycarbonyl-ethoxycarbonyl-methylamino)-1,4'-bipiperidinyl-1'-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 2106520노트

반응식

HRID 2106520 반응식
CN(C(ON1N=NC2C=C[CH:14]=[CH:15][C:10]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:23](N(CC)CC)[CH3:24].[O:30]=[C:31]1[N:37]([CH:38]2[CH2:43][CH2:42][N:41]([C:44]([O:46][C@@H:47]([C:61](O)=[O:62])[CH2:48][C:49]3[CH:54]=[C:53]([C:55]([F:58])([F:57])[F:56])[C:52]([NH2:59])=[C:51]([Cl:60])[CH:50]=3)=[O:45])[CH2:40][CH2:39]2)[CH2:36][CH2:35][C:34]2[CH:64]=[CH:65][CH:66]=[CH:67][C:33]=2[NH:32]1.[N:68]1([CH:88]2[CH2:93][CH2:92][NH:91][CH2:90][CH2:89]2)[CH2:73][CH2:72][CH:71]([N:74]([CH2:82][C:83]([O:85]CC)=[O:84])[C:75]([O:77]C(C)(C)C)=[O:76])[CH2:70][CH2:69]1.[CH3:94]N(C=O)C>>[O:30]=[C:31]1[N:37]([CH:38]2[CH2:39][CH2:40][N:41]([C:44]([O:46][C@H:47]([CH2:48][C:49]3[CH:54]=[C:53]([C:55]([F:57])([F:58])[F:56])[C:52]([NH2:59])=[C:51]([Cl:60])[CH:50]=3)[C:61]([N:91]3[CH2:92][CH2:93][CH:88]([N:68]4[CH2:69][CH2:70][CH:71]([N:74]([C:75]([O:77][CH2:23][CH3:24])=[O:76])[CH2:82][C:83]([O:85][C:15]([CH3:14])([CH3:10])[CH3:94])=[O:84])[CH2:72][CH2:73]4)[CH2:89][CH2:90]3)=[O:62])=[O:45])[CH2:42][CH2:43]2)[CH2:36][CH2:35][C:34]2[CH:64]=[CH:65][CH:66]=[CH:67][C:33]=2[NH:32]1

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57807378Ethyl([1,4']bipiperidinyl-4-yl-tert-butoxycarbonyl-amino)-acetateHCID 58202073(R)-2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

생성물 1

HCID 86611123(R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-(tert-butoxycarbonyl-ethoxycarbonyl-methylamino)-1,4'-bipiperidinyl-1'-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

실험 절차

128 mg (0.40 mmol) TBTU and 56 μL (0.40 mmol) triethylamine were added to a solution of 200 mg (0.36 mmol) (R)-2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 2 mL DMF and stirred for 10 min at RT. 148 mg (0.40 mmol) ethyl ([1,4′]bipiperidinyl-4-yl-tert-butoxycarbonyl-amino)-acetate (Amine A6) were added to the reaction mixture and this was stirred overnight at RT. The reaction solution was evaporated down i. vac., the residue was taken up in EtOAc, the precipitate formed was suction filtered and dried. The product was reacted further without purification.

후처리

  1. stirringthis was stirred overnight at RT
  2. customThe reaction solution was evaporated down i
  3. customthe precipitate formed
  4. filtrationfiltered
  5. customdried
  6. customThe product was reacted further without purification

출처 및 근거

ORD 기록
ord-81641685408c48beb298c10793a6ab76
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579341B2

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