(4-{4-[5-(6-Benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-benzyl)-carbamic acid tert-butyl ester → HCID 136388310, compound

HRID 19602Notes

Reaction equation

HRID 19602 reaction equation
[C:1]([O:5][C:6](=[O:52])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:51])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[N:29]4[N:30]=[CH:31][CH:32]=[C:28]4[CH:27]=[C:26]([C:33]4[CH:42]=[CH:41][C:40]5[C:35](=[CH:36][CH:37]=[C:38]([O:43]CC6C=CC=CC=6)[CH:39]=5)[CH:34]=4)[N:25]=3)=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.[Pd]>[C:1]([O:5][C:6](=[O:52])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:51])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[N:29]4[N:30]=[CH:31][CH:32]=[C:28]4[CH:27]=[C:26]([C:33]4[CH:42]=[CH:41][C:40]5[C:35](=[CH:36][CH:37]=[C:38]([OH:43])[CH:39]=5)[CH:34]=4)[N:25]=3)=[CH:19][CH:18]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67319336(4-{4-[5-(6-Benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-benzyl)-carbamic acid tert-butyl ester2×

Product 1

HCID 136388310HCID 136388310, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (4-{4-[5-(6-benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-benzyl)-carbamic acid tert-butyl ester (compound A2)(750 mg) and Pd/C (10%, 100 mg) in dioxane (100 ml) is hydrogenated (1.1 bar) at 80° C. for 3 days. The reaction mixture is filtered and the filtrate is evaporated. After silica gel flash chromatography the product is obtained as colorless solid in 48% yield.

Workup

  1. customat 80° C.
  2. customfor 3 days
  3. filtrationThe reaction mixture is filtered
  4. customthe filtrate is evaporated
  5. customAfter silica gel flash chromatography the product is obtained as colorless solid in 48% yield

Sources & evidence

ORD record
ord-974a081e77a3417da4398a24d196880c
Source dataset
uspto-grants-2010_06
Patent number
US07745446B2

Reaction notes

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