ethyl 7-(4-(((R)-5-(benzyloxy)hexyl)oxy)-4-methylpiperidin-1-yl)-6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate → ethyl 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4-(((R)-5-hydroxyhexyl)oxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate

HRID 921145Notes

Reaction equation

HRID 921145 reaction equation
C([O:8][C@H:9]([CH3:48])[CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1([CH3:47])[CH2:20][CH2:19][N:18]([C:21]2[N:26]3[N:27]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:29]=[C:25]3[N:24]=[C:23]([CH3:35])[C:22]=2[C@H:36]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:17][CH2:16]1)C1C=CC=CC=1.[H][H]>CCO.[Pd]>[C:43]([O:42][C@@H:36]([C:22]1[C:23]([CH3:35])=[N:24][C:25]2[N:26]([N:27]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:29]=2)[C:21]=1[N:18]1[CH2:19][CH2:20][C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([OH:8])[CH3:48])([CH3:47])[CH2:16][CH2:17]1)[C:37]([O:39][CH2:40][CH3:41])=[O:38])([CH3:44])([CH3:45])[CH3:46]

Participants

5

Reactant 2

HCID 118307152ethyl 7-(4-(((R)-5-(benzyloxy)hexyl)oxy)-4-methylpiperidin-1-yl)-6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 118307156ethyl 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4-(((R)-5-hydroxyhexyl)oxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 7-(4-(((R)-5-(benzyloxy)hexyl)oxy)-4-methylpiperidin-1-yl)-6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (1.7 g, 2.55 mmol) in EtOH (25 mL) was added 10% Pd/C (0.271 g, 0.255 mmol) and the resulting mixture was stirred under balloon hydrogen atmosphere for 5 h. Mixture was then filtered and concentrated to afford ethyl 6-((S)-1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-(4-(((R)-5-hydroxyhexyl)oxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (1.2 g, 2.081 mmol, 82% yield) as viscous oil. LCMS (M+H)=577.3. Used as is in the next step without further purification.

Workup

  1. filtrationMixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7f6fb772620f4b639d55cf0956df64e3
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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