Ethanol → HCID 45256713, compound

HRID 906439Notes

Reaction equation

HRID 906439 reaction equation
[Si]([O:8][CH2:9][C:10]([CH3:53])([CH3:52])[CH2:11][N:12]1[CH:21]=[C:20]([CH:22]([N:24]2[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]2)[CH3:23])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:37]3[CH:42]=[C:41]([C:43](=[O:48])[NH:44][CH:45]4[CH2:47][CH2:46]4)[CH:40]=[C:39]([F:49])[C:38]=3[CH3:50])[CH:18]=2)[C:13]1=[O:51])(C(C)(C)C)(C)C.C(O)C>Cl.O1CCOCC1>[CH:45]1([NH:44][C:43](=[O:48])[C:41]2[CH:42]=[C:37]([C:17]3[CH:18]=[C:19]4[C:14](=[CH:15][CH:16]=3)[C:13](=[O:51])[N:12]([CH2:11][C:10]([CH3:53])([CH3:52])[CH2:9][OH:8])[CH:21]=[C:20]4[CH:22]([N:24]3[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]3)[CH3:23])[C:38]([CH3:50])=[C:39]([F:49])[CH:40]=2)[CH2:47][CH2:46]1

Participants

5

Reactant 2

HCID 702EthanolHCID 67391278HCID 67391278, compound

Product 1

HCID 45256713HCID 45256713, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 4-(1-{2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-1-oxo-1,2-dihydroisoquinolin-4-yl}ethyl)piperazine-1-carboxylate (Example 38c, 80 mg) in 4 M HCl in dioxane (1 mL) and ethanol (3 mL) was stirred overnight at room temperature before the volatiles were removed in vacuo. The crude material was dissolved in methanol (2 mL) and loaded onto a 10 g SCX cartridge. The impurities were washed through with methanol (50 mL) and discarded. The product was eluted with 1 N methanolic ammonia (50 mL) and evaporated in vacuo to afford the title product (58 mg).

Workup

  1. customwere removed in vacuo
  2. dissolutionThe crude material was dissolved in methanol (2 mL)
  3. washThe impurities were washed through with methanol (50 mL)
  4. washThe product was eluted with 1 N methanolic ammonia (50 mL)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-90fd188961b848f4bd1d95807792c535
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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