HCID 57999660, compound → HCID 42642455, compound

HRID 600317Notes

Reaction equation

HRID 600317 reaction equation
[C:1]([C@@H:3]([NH:19][C:20]([C@@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][N:23]1C(OC(C)(C)C)=O)=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)#[N:2]>C(O)=O>[C:1]([C@@H:3]([NH:19][C:20]([C@@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][NH:23]1)=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)#[N:2]

Participants

3

Reactant 1

HCID 57999660HCID 57999660, compound

Product 1

HCID 42642455HCID 42642455, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(S)-tert-Butyl 2-((S)-1-cyano-2-(4-(6-cyanopyridin-3-yl)phenyl)ethylcarbamoyl)-piperidine-1-carboxylate (0.074 g) in formic acid (3 mL) was heated at 50° C. for 10 min. The mixture was evaporated, dissolved in methanol and applied to a 10 g SCX column. The column was washed with methanol then eluted with 10% ammonia in methanol. The eluate was evaporated. The residue was triturated with isopropanol and the solid collected, washed with a little isopropanol and diethyl ether then dried to leave the title compound as a solid (0.048 g).

Workup

  1. customThe mixture was evaporated
  2. dissolutiondissolved in methanol
  3. washThe column was washed with methanol
  4. washthen eluted with 10% ammonia in methanol
  5. customThe eluate was evaporated
  6. customThe residue was triturated with isopropanol
  7. customthe solid collected
  8. washwashed with a little isopropanol and diethyl ether
  9. customthen dried

Sources & evidence

ORD record
ord-ea265934f3f64f16b7ad84dbd7b63ac8
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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