Triethylamine → N-{4-[3-cyclopropylmethyl-1-(2-fluorobenzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-6,N-dimethyl-nicotinamide

HRID 720655Notes

Reaction equation

HRID 720655 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH:11]1([CH2:14][N:15]2[C:23]3[N:22]=[C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([NH:31][CH3:32])=[CH:27][CH:26]=4)[NH:20][C:19]=3[C:18](=[O:33])[N:17]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[F:41])[C:16]2=[O:42])[CH2:13][CH2:12]1.C(N(CC)CC)C>>[CH:11]1([CH2:14][N:15]2[C:23]3[N:22]=[C:21]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([N:31]([CH3:32])[C:6](=[O:8])[C:5]5[CH:9]=[CH:10][C:2]([CH3:1])=[N:3][CH:4]=5)=[CH:29][CH:30]=4)[NH:20][C:19]=3[C:18](=[O:33])[N:17]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[F:41])[C:16]2=[O:42])[CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 1378606-Methylnicotinic acidHCID 218916913-Cyclopropylmethyl-8-[4-(methylamino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydropurine-2,6-dione

Product 1

HCID 10007787N-{4-[3-cyclopropylmethyl-1-(2-fluorobenzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-6,N-dimethyl-nicotinamide

Procedure

This compound was prepared by a method similar to that described in example 79 except that commercially available 6-methylnicotinic acid was used in place of N-acetyl-6-amino-2-pyridine carboxylic acid, the reaction was performed using 0.54 equivalents of 3-cyclopropylmethyl-8-[4-(methylamino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydropurine-2,6-dione and 1.2 equivalents of triethylamine were added as the final reagent to the reaction mixture. The product was purified by chromatography using silica gel eluted with 95:5 chloroform/methanol followed by crystallization from acetonitrile. MS, m/z(M+)=553.2365.

Workup

  1. customThis compound was prepared by a method similar to
  2. customThe product was purified by chromatography
  3. washeluted with 95:5 chloroform/methanol
  4. customfollowed by crystallization from acetonitrile

Sources & evidence

ORD record
ord-6151cec836c945619ef97fdcc19a833a
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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