HCID 10102032, compound → HCID 10032702, compound

HRID 736934Notes

Reaction equation

HRID 736934 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH2:12][C@@H:13]([NH:38][C:39]([N:41]2[CH2:46][CH2:45][CH:44]([N:47]3[CH2:53][CH2:52][C:51]4[CH:54]=[CH:55][CH:56]=[CH:57][C:50]=4[NH:49][C:48]3=[O:58])[CH2:43][CH2:42]2)=[O:40])[C:14]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:27][CH2:26][N:25](C(OCC4C=CC=CC=4)=O)[CH2:24][CH2:23]3)[CH2:18][CH2:17]2)=[O:15])=[CH:4][C:3]=1[Cl:59]>[Ni].CO>[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH2:12][C@@H:13]([NH:38][C:39]([N:41]2[CH2:46][CH2:45][CH:44]([N:47]3[CH2:53][CH2:52][C:51]4[CH:54]=[CH:55][CH:56]=[CH:57][C:50]=4[NH:49][C:48]3=[O:58])[CH2:43][CH2:42]2)=[O:40])[C:14](=[O:15])[N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)[CH2:18][CH2:17]2)=[CH:4][C:3]=1[Cl:59]

Participants

4

Reactant 1

HCID 10102032HCID 10102032, compound

Product 1

HCID 10032702HCID 10032702, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 600 mg (0.72 mmol) benzyl 4-[1-((R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-carbonyl]-amino}-propionyl)-piperidin-4-yl]-piperazin-1-carboxylate (Example 7.4) and 200 mg Raney nickel in 50 mL MeOH were hydrogenated at RT and 50 psi of H2 for 12 h. The catalyst was filtered off, the solvent evaporated down i.vac. and the residue purified by HPLC.

Workup

  1. customwere hydrogenated at RT
  2. filtrationThe catalyst was filtered off
  3. customthe solvent evaporated down i.vac
  4. customand the residue purified by HPLC

Sources & evidence

ORD record
ord-c433ebca0b1642a6803fa8cea05d858f
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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