N-methyl-2-pyrrolidone → 1-[(3-Cyanopyridin-2-yl)methyl]-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-phthalimidopiperidin-1-yl)-xanthine

HRID 44905Notes

Reaction equation

HRID 44905 reaction equation
[C:1]([C:3]1[C:4]([CH2:9][N:10]2[C:19](=[O:20])[C:18]3[N:17]([CH2:21][C:22]#[C:23][CH3:24])[C:16](Br)=[N:15][C:14]=3[N:13]([CH3:26])[C:11]2=[O:12])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].C([C@H]([C@@H](C(O)=O)O)O)(O)=O.[C:37]1(=[O:53])[N:41]([CH:42]2[CH2:47][CH2:46][CH2:45][NH:44][CH2:43]2)[C:40](=[O:48])[C:39]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:38]12.CN1CCCC1=O.C(N(C(C)C)CC)(C)C>CO.O>[C:1]([C:3]1[C:4]([CH2:9][N:10]2[C:19](=[O:20])[C:18]3[N:17]([CH2:21][C:22]#[C:23][CH3:24])[C:16]([N:44]4[CH2:45][CH2:46][CH2:47][C@@H:42]([N:41]5[C:40](=[O:48])[C:39]6=[CH:49][CH:50]=[CH:51][CH:52]=[C:38]6[C:37]5=[O:53])[CH2:43]4)=[N:15][C:14]=3[N:13]([CH3:26])[C:11]2=[O:12])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 167265441-[(3-Cyano-pyridin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthineHCID 667041493-(Phthalimido)piperidine d-tartrate

Product 1

HCID 167266001-[(3-Cyanopyridin-2-yl)methyl]-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-phthalimidopiperidin-1-yl)-xanthine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

230 g (0.557 mol) of 1-[(3-cyanopyridin-2-yl)methyl]-3-methyl-7-(2-butin-1-yl)-8-bromoxanthine, 318 g (0.835 mol) of 3-(phthalimido)piperidine D-tartrate and 1.15 liters of N-methyl-2-pyrrolidone are initially charged in the reactor. The reactor contents are heated to 140° C. After the temperature has been attained, 478 ml (2.78 mol) of diisopropylethylamine are metered in within 20 minutes and the reaction mixture is subsequently stirred at 140° C. for 2 hours. Subsequently, the reaction mixture is cooled to 75° C. and diluted with 720 ml of methanol. Afterwards, 2.7 liters of water are added at 68-60° C. and the mixture is cooled to 25° C. The product is filtered off and washed with 2 liters of water. Drying is effected at 70° C. in a drying cabinet under inertization.

Workup

  1. customare metered in within 20 minutes
  2. temperatureSubsequently, the reaction mixture is cooled to 75° C.
  3. temperaturethe mixture is cooled to 25° C
  4. filtrationThe product is filtered off
  5. washwashed with 2 liters of water
  6. customDrying
  7. customis effected at 70° C. in a drying cabinet under inertization

Sources & evidence

ORD record
ord-05ad441eceee4e91b38ef5129ebaf7de
Source dataset
uspto-grants-2013_09
Patent number
US08541450B2

Reaction notes

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