Hydrochloric Acid → HCID 68930959, compound

HRID 32054Notes

Reaction equation

HRID 32054 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([NH:13][C:14](=[O:37])[CH2:15][CH:16]([NH:23][S:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)(=[O:26])=[O:25])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1)#[N:2].Cl.CO.Cl>CO.[OH-].[OH-].[Pd+2]>[NH2:2][CH2:1][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([NH:13][C:14](=[O:37])[CH2:15][CH:16]([NH:23][S:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)(=[O:26])=[O:25])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21893726Hydrochloride methanolHCID 68934380HCID 68934380, compound

Product 1

HCID 68930959HCID 68930959, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

N-(7-Cyano-chroman-4-yl)-3-(naphthalen-2-ylsulfonylamino)-3-phenyl-propionamide (Example 1, Step F) (30 mg, 0.06 mmol) and Pd(OH)2 (6 mg) was added in MeOH (10 mL), followed by adding 1.0 mL of 3.0 M HCl-MeOH. The solution was purged with N2, then sealed with H2 (50 psi) and shaken overnight until the reduction was completed. The solution was filtered, and concentrated to near dryness in vacuo. The crude compound was purified by precipitation in EtOAc-Et2O to provide the HCl salt as a white solid mixture of diastereomer. MS (ESI) 516 (M+H)+.

Workup

  1. customThe solution was purged with N2
  2. customsealed with H2 (50 psi)
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. customThe crude compound was purified by precipitation in EtOAc-Et2O
  6. customto provide

Sources & evidence

ORD record
ord-e6529eadb5c44e92ab811faaa1311c44
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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