Water → HCID 68602008, compound

HRID 1454944Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:40])[CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]#[C:23][CH3:24])[C:16]([N:25]3[CH2:30][CH2:29][CH2:28][CH:27]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:26]3)=[N:15][C:14]=2[N:13]([CH3:39])[C:11]1=[O:12].[C:41](=[O:44])([O-])[O-:42].[K+].[K+].O>CN(C)C=O>[C:35]([O:42][C:41]([NH:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:40])[CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]#[C:23][CH3:24])[C:16]([N:25]3[CH2:30][CH2:29][CH2:28][CH:27]([NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:26]3)=[N:15][C:14]=2[N:13]([CH3:39])[C:11]1=[O:12])=[O:44])([CH3:38])([CH3:37])[CH3:36]

Participants

Conditions

Temperature: 55 °C

Procedure

187 mg of tert.-butyl 2-bromo-ethyl-carbaminate are added to 400 mg of 1-[2-(2-hydroxy-phenyl)-2-oxo-ethyl]-3-methyl-7-(2-butyn-1-yl)-8-[3-(tert.-butyloxycarbonyl-amino)-piperidin-1-yl]-xanthine and 150 mg of potassium carbonate in 6 ml N,N-dimethylformamide and the reaction mixture is stirred overnight at 55° C. Then a further 90 mg of tert.-butyl 2-bromo-ethyl-carbaminate are added. After another eight hours at 55° C. the reaction is complete. The cooled reaction mixture is combined with water, the precipitate formed is suction filtered, washed with water and dried.

Workup

additionThen a further 90 mg of tert.-butyl 2-bromo-ethyl-carbaminate are added
waitAfter another eight hours at 55° C. the reaction is complete
customThe cooled reaction mixture
customthe precipitate formed
filtrationfiltered
washwashed with water
customdried

Sources & evidence

ORD record: ord-9126d49acb374e919966fbe5c774822b
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482337B2

Reaction notes

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