Sodium → HCID 57617466, compound

HRID 1686162Notes

Reaction equation

HRID 1686162 reaction equation
[CH3:1][CH:2]([CH2:53][CH3:54])[C@H:3]([NH:14][C:15]([C@:17]1([NH:34][C:35](=[O:52])[C@@H:36]([NH:41][C:42](=[O:51])[CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[F:50])[CH:37]([CH3:40])[CH2:38][CH3:39])[CH2:29][C:28]2[C:27]3[C:22](=[C:23]([C:30]([F:33])([F:32])[F:31])[CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]=2[CH2:19][CH2:18]1)=[O:16])[C:4](=S)[NH:5][CH2:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[Na]>C1COCC1.CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:1][CH:2]([CH2:53][CH3:54])[C@H:3]([NH:14][C:15]([C@:17]1([NH:34][C:35](=[O:52])[C@@H:36]([NH:41][C:42](=[O:51])[CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[F:50])[CH:37]([CH3:40])[CH2:38][CH3:39])[CH2:29][C:28]2[C:27]3[C:22](=[C:23]([C:30]([F:33])([F:32])[F:31])[CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]=2[CH2:19][CH2:18]1)=[O:16])[CH2:4][NH:5][CH2:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 25027349HCID 25027349, compound

Product 1

HCID 57617466HCID 57617466, compound

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

0.050 g (0.06 mmol) of (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-2-methyl-1-[(tetrahydro-pyran-4-ylmethyl)-thiocarbamoyl]-butyl}-amide were dissolved in 7 mL of THF/Methanol (1:1). 0.123 g (0.52 mmol) of nickel(II)chloride hexahydrate were added at room temperature. The mixture was stirred for 10 min at this temperature. At 0° C. 0.059 g (1.55 mmol) sodium borhydrate were added. Stirring was continued for 18 h at room temperature. The mixture was filtered over silica gel and the silica gel layer was washed with MeOH. The filtrate and washes were combined, concentrated and the residue purified by HPLC.

Workup

  1. customAt 0° C
  2. stirringStirring
  3. waitwas continued for 18 h at room temperature
  4. filtrationThe mixture was filtered over silica gel
  5. washthe silica gel layer was washed with MeOH
  6. concentrationconcentrated
  7. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-802fa1949be948d2ba6b5c3181c49aad
Source dataset
uspto-grants-2012_04
Patent number
US08148546B2

Reaction notes

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