4-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid 1-benzyl-pyrrolidin-3-yl ester → 4-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid pyrrolidin-3-yl ester

HRID 448596Notes

Reaction equation

HRID 448596 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]([N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[C:27]([N:29]4[C:37]5[C:32](=[CH:33][C:34]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:35][CH:36]=5)[CH2:31][CH2:30]4)[N:26]=[CH:25][N:24]=3)[CH2:18][CH2:17]2)=[O:15])[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]([N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[C:27]([N:29]4[C:37]5[C:32](=[CH:33][C:34]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:35][CH:36]=5)[CH2:31][CH2:30]4)[N:26]=[CH:25][N:24]=3)[CH2:18][CH2:17]2)=[O:15])[CH2:9]1

Participants

5

Reactant 2

HCID 669006884-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid 1-benzyl-pyrrolidin-3-yl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 498486594-[6-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid pyrrolidin-3-yl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

23a (0.2 mmol) and 30 mg of Pd/C in 3 mL of ethanol were stirred under 60 psi of hydrogen for 12 h. The suspension was filtered on celite with ethanol, evaporated and purified by preparative HPLC to afford 23-1, LCMS 488.1 (MH+). tR=5.21 (Method 5).

Workup

  1. filtrationThe suspension was filtered on celite with ethanol
  2. customevaporated
  3. custompurified by preparative HPLC
  4. customto afford 23-1, LCMS 488.1 (MH+)

Sources & evidence

ORD record
ord-bfd4dd1862b34fd6be81010b797df355
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

Loading…