HCID 59344858, compound → HCID 59165999, compound

HRID 2420853Notes

Reaction equation

HRID 2420853 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:17]2([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]4[CH:34]=[CH:33][C:32]([S:35]([N:38]5[CH2:42][CH2:41][CH2:40][C@@H:39]5[CH2:43][OH:44])(=[O:37])=[O:36])=[CH:31][CH:30]=4)[N:24]=3)=[O:21])[CH2:19][CH2:18]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:17]2([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]4[CH:34]=[CH:33][C:32]([S:35]([N:38]5[CH2:42][CH2:41][CH2:40][C@@H:39]5[CH2:43][OH:44])(=[O:37])=[O:36])=[CH:31][CH:30]=4)[N:24]=3)=[O:21])[CH2:18][CH2:19]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

5

Reactant 2

HCID 59344858HCID 59344858, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59165999HCID 59165999, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R)-1-(3-(Benzyloxy)-4-methoxyphenyl)-N-(6-(4-(2-(hydroxymethyl)pyrrolidin-1-ylsulfonyl)phenyl)pyridin-2-yl)cyclopropanecarboxamide (28 mg, 0.046 mmol) was dissolved in ethanol (3 mL). Palladium on charcoal (10%, 20 mg) was added and the reaction was stirred overnight under 1 atm of hydrogen. The catalyst was filtered off and the product was isolated by silica gel chromatography (50-80% EtOAc in hexane) to provide (R)-1-(3-hydroxy-4-methoxyphenyl)-N-(6-(4-(2-(hydroxymethyl)pyrrolidin-1-ylsulfonyl)phenyl)pyridin-2-yl)cyclopropanecarboxamide (8 mg, 34%). ESI-MS m/z calc. 523.4, found 524.3 (M+1)+. Retention time of 3.17 minutes.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe product was isolated by silica gel chromatography (50-80% EtOAc in hexane)

Sources & evidence

ORD record
ord-87d75c41546b4081921fee74c0e286dd
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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