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 2106520Notes

Reaction equation

HRID 2106520 reaction equation
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

Participants

6

Reactant 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

Product 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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-81641685408c48beb298c10793a6ab76
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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