HCID 86717554, compound → HCID 86717555, compound

HRID 712101Notes

Reaction equation

HRID 712101 reaction equation
[C:1]([CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]2[C:16]([N+:17]([O-])=O)=[CH:15][N:14]=[C:13]3[CH:20]=[CH:21][S:22][C:12]=23)[CH2:6][C@H:5]1[NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)#[N:2]>[Pd].CO>[NH2:17][C:16]1[C:11]([NH:10][C@@H:7]2[CH2:6][C@@H:5]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:4]([CH2:3][C:1]#[N:2])[CH2:9][CH2:8]2)=[C:12]2[S:22][CH:21]=[CH:20][C:13]2=[N:14][CH:15]=1

Participants

4

Reactant 1

HCID 86717554HCID 86717554, compound

Product 1

HCID 86717555HCID 86717555, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl {(1R,2R,5S)-2-(cyanomethyl)-5-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}carbamate (28 mg, 0.060 mmol) and 10% palladium on carbon (7.0 mg) in methanol (0.44 mL) was stirred under an atmosphere of H2 (balloon) for 3 h. The mixture was filtered and concentrated to give 26 mg of the desired product. LCMS calculated for C23H26N5O2S (M+H)+: m/z=436.2. Found: 436.0.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d0ae744ef33245f898499faf0f0f7913
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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