HCID 68603211, compound → HCID 178448603, compound

HRID 641360Notes

Reaction equation

HRID 641360 reaction equation
[NH2:1][C:2]1[CH:42]=[CH:41][CH:40]=[CH:39][C:3]=1[CH2:4][NH:5][C:6](=O)[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[N:15]([CH2:19][C:20]#[C:21][CH3:22])[C:14]([N:23]3[CH2:28][CH2:27][CH2:26][CH:25]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:24]3)=[N:13][C:12]=2[N:11]([CH3:37])[C:9]1=[O:10]>C(O)(=O)C>[N:1]1[C:2]2[C:3](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:4][NH:5][C:6]=1[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[N:15]([CH2:19][C:20]#[C:21][CH3:22])[C:14]([N:23]3[CH2:28][CH2:27][CH2:26][CH:25]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:24]3)=[N:13][C:12]=2[N:11]([CH3:37])[C:9]1=[O:10]

Participants

3

Reactant 1

HCID 68603211HCID 68603211, compound

Product 1

HCID 178448603HCID 178448603, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 280 mg of 1-[2-(2-amino-benzylamino)-2-oxo-ethyl]-3-methyl-7-(2-butyn-1-yl)-8-[3-(tert.-butyloxycarbonyl-amino)-piperidin-1-yl]-xanthine and 4 ml glacial acetic acid is heated to boiling for two hours. Then the reaction mixture is evaporated down and the flask residue is purified through a column of aluminium oxide (activity stage 11) with methylene chloride/ethyl acetate/methanol (5:5:0 to 5:4:1) as eluant. In addition to the desired 1-[(3,4-dihydro-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[3-(tert.-butyloxycarbonyl-amino)-piperidin-1-yl]-xanthine, deprotected 1-[(3,4-dihydro-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-(3-amino-piperidin-1-yl)-xanthine is also obtained.

Workup

  1. temperatureis heated
  2. customThen the reaction mixture is evaporated down
  3. customthe flask residue is purified through a column of aluminium oxide (activity stage 11) with methylene chloride/ethyl acetate/methanol (5:5:0 to 5:4:1) as eluant
  4. additionIn addition to the desired 1-[(3,4-dihydro-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[3-(tert.-butyloxycarbonyl-amino)-piperidin-1-yl]-xanthine, deprotected 1-[(3,4-dihydro-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-(3-amino-piperidin-1-yl)-xanthine
  5. customis also obtained

Sources & evidence

ORD record
ord-8979cfe49cc84f7588e98adc6e8221cf
Source dataset
uspto-grants-2010_04
Patent number
US07696212B2

Reaction notes

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