N-[(4-benzylmorpholin-2-yl)methyl]-7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxamide → 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-(morpholin-2-ylmethyl)-2,3-dihydrobenzofuran-4-carboxamide

HRID 2364673Notes

Reaction equation

HRID 2364673 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH:15][C:16]([C:18]2[CH:19]=[CH:20][C:21]([NH:27][C:28]3[N:37]=[CH:36][C:35]4[N:34]([CH3:38])[C:33](=[O:39])[C@@H:32]([CH2:40][CH3:41])[N:31]([CH:42]5[CH2:46][CH2:45][CH2:44][CH2:43]5)[C:30]=4[N:29]=3)=[C:22]3[O:26][CH2:25][CH2:24][C:23]=23)=[O:17])[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH:42]1([N:31]2[C:30]3[N:29]=[C:28]([NH:27][C:21]4[CH:20]=[CH:19][C:18]([C:16]([NH:15][CH2:14][CH:10]5[O:11][CH2:12][CH2:13][NH:8][CH2:9]5)=[O:17])=[C:23]5[C:22]=4[O:26][CH2:25][CH2:24]5)[N:37]=[CH:36][C:35]=3[N:34]([CH3:38])[C:33](=[O:39])[C@H:32]2[CH2:40][CH3:41])[CH2:43][CH2:44][CH2:45][CH2:46]1

Participants

5

Reactant 2

HCID 68107811N-[(4-benzylmorpholin-2-yl)methyl]-7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 681078727-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-(morpholin-2-ylmethyl)-2,3-dihydrobenzofuran-4-carboxamideYield 101.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-[(4-benzylmorpholin-2-yl)methyl]-7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxamide 2e (0.19 g, 0.30 mmol) was dissolved in 30 mL of methanol followed by the addition of palladium/carbon (40 mg, 10%), filled with hydrogen two times. The reaction solution was stirred for 2 hours and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-(morpholin-2-ylmethyl)-2,3-dihydrobenzofuran-4-carboxamide 2f (163 mg) as a white solid, which was used in the next step without further furification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a5a448cd7a7f4190984390cd87c17359
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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