Diisopropylethylamine → (2s)-2-Benzyloxycarbonylamino-3-(6-(4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl)-purin-9-yl)-propionic acid tert-butyl ester

HRID 351649Notes

Reaction equation

HRID 351649 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:16]=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][NH:14]3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[C:26]([O:30][C:31](=[O:55])[C@@H:32]([NH:44][C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH2:33][N:34]1[CH:42]=[N:41][C:40]2[C:35]1=[N:36][CH:37]=[N:38][C:39]=2Cl)([CH3:29])([CH3:28])[CH3:27]>CN(C)C=O>[C:26]([O:30][C:31](=[O:55])[C@@H:32]([NH:44][C:45]([O:47][CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)=[O:46])[CH2:33][N:34]1[CH:42]=[N:41][C:40]2[C:35]1=[N:36][CH:37]=[N:38][C:39]=2[N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[CH:9][C:10]3[CH2:11][CH2:12][CH2:13][NH:14][C:15]=3[N:16]=2)[CH2:3][CH2:2]1)([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11384926(s)-2-Benzyloxycarbonylamino-3-(6-chloro-purin-9-yl)-propionic acid tert-butyl esterHCID 113903267-(4-Piperidinyl)-1,2,3,4-tetrahydro[1,8]naphthyridine

Product 1

HCID 11422135(2s)-2-Benzyloxycarbonylamino-3-(6-(4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl)-purin-9-yl)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.44 g of the compound of step c) were dissolved in 5 ml of anhydrous dimethylformamide. 0.7 ml of N,N-diisopropylethylamine were added together with 0.58 g of (S)-2-benzyloxycarbonylamino-3-(6-chloro-purin-9-yl)-propionic acid tert-butyl ester, and the mixture was stirred at ambient temperature overnight. Thin layer chromatographic control exhibited only incomplete reaction. Stirring was therefore continued for 6 hours at 40° C. until the reaction was complete. The solvent was removed in vacuo and the residue was dissolved in dichloromethane and washed twice with water. The organic phase was dried with anhydrous magnesium sulfate and, after filtration, concentrated in vacuo. The raw material was chromatographed on silica gel with ethyl acetate and ethyl acetate/methanol (1:10). Yield: 224 mg.

Workup

  1. customreaction
  2. stirringStirring
  3. waitwas therefore continued for 6 hours at 40° C. until the reaction
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washwashed twice with water
  7. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  8. filtrationafter filtration
  9. concentrationconcentrated in vacuo
  10. customThe raw material was chromatographed on silica gel with ethyl acetate and ethyl acetate/methanol (1:10)

Sources & evidence

ORD record
ord-714be0dd4a854c1a8233c6b10460d9c2
Source dataset
uspto-grants-2004_06
Patent number
US06743800B1

Reaction notes

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