Triethylamine → HCID 10076306, compound

HRID 720661Notes

Reaction equation

HRID 720661 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.BrN1C(=O)CCC1=O.[CH:19]1([CH2:22][N:23]2[C:31]3[N:30]=[C:29]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([NH:39][CH3:40])=[CH:35][CH:34]=4)[NH:28][C:27]=3[C:26](=[O:41])[N:25]([CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[F:49])[C:24]2=[O:50])[CH2:21][CH2:20]1.C(N(CC)CC)C>>[CH:19]1([CH2:22][N:23]2[C:31]3[N:30]=[C:29]([CH2:32][C:33]4[CH:34]=[CH:35][C:36]([N:39]([CH3:40])[C:4](=[O:6])[C:3]5[CH:7]=[CH:8][CH:9]=[N:10][C:2]=5[CH3:1])=[CH:37][CH:38]=4)[NH:28][C:27]=3[C:26](=[O:41])[N:25]([CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[F:49])[C:24]2=[O:50])[CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 6433732-Methylnicotinic acidHCID 218916913-Cyclopropylmethyl-8-[4-(methylamino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydropurine-2,6-dione

Product 1

HCID 10076306HCID 10076306, compoundYield 34%

Procedure

This compound was prepared by a method similar to that described in example 79 except that 2-methylnicotinic acid (Aldrich) was used in place of N-acetyl-6-amino-2-pyridine carboxylic acid, N-bromosuccinimide was used in place of N-chlorosuccinimide, the reaction was performed using 0.66 equivalents of 3-cyclopropylmethyl-8-[4-(methylamino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydropurine-2,6-dione and 1 equivalent of triethylamine was added as the final reagent to the reaction mixture. Purification was performed by chromatography using silica eluted with 95:5 ethyl acetate/methanol to give the product as a light brown solid (34%). MS, M+H)=553.2361.

Workup

  1. customThis compound was prepared by a method similar to
  2. customPurification
  3. washeluted with 95:5 ethyl acetate/methanol

Sources & evidence

ORD record
ord-a3f58d23188d4841b3f5bb8303b5f7c1
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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