Oxalic Acid → 3-[4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-acrylic acid tert-butyl ester oxalate

HRID 1773873Notes

Reaction equation

HRID 1773873 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH:7]=[CH:8][C:9]1[N:18]=[C:17]2[N:11]([CH2:12][CH2:13][C:14]3[CH:30]=[CH:29][CH:28]=[CH:27][C:15]=3[CH:16]2[O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>CC(C)=O>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[C:1]([O:5][C:6](=[O:31])[CH:7]=[CH:8][C:9]1[N:18]=[C:17]2[N:11]([CH2:12][CH2:13][C:14]3[CH:30]=[CH:29][CH:28]=[CH:27][C:15]=3[CH:16]2[O:19][CH:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 867039593-[4-(1-methyl piperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-acrylic acid tert-butyl ester

Product 1

HCID 1317347143-[4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-acrylic acid tert-butyl ester oxalate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-[4-(1-methyl piperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-acrylic acid tert-butyl ester is dissolved in acetone (1.7 mL) and oxalic acid (1 equivalent) is added. Acetone is removed under reduced pressure to afford the compound as an oxalate.

Workup

  1. customAcetone is removed under reduced pressure

Sources & evidence

ORD record
ord-375542cd0d124c88bdfa3367ba819d7b
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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