6-Cyanopyridine-3-carboxylic acid → HCID 58739242, compound

HRID 720660Notes

Reaction equation

HRID 720660 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][N:4]=1)#[N:2].[CH:12]1([CH2:15][N:16]2[C:24]3[N:23]=[C:22]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([NH:32][CH3:33])=[CH:28][CH:27]=4)[NH:21][C:20]=3[C:19](=[O:34])[N:18]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[F:42])[C:17]2=[O:43])[CH2:14][CH2:13]1>CN(C)C1C=CN=CC=1>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:32]([C:29]2[CH:30]=[CH:31][C:26]([CH2:25][C:22]3[NH:21][C:20]4[C:19](=[O:34])[N:18]([CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=5[F:42])[C:17](=[O:43])[N:16]([CH2:15][CH:12]5[CH2:14][CH2:13]5)[C:24]=4[N:23]=3)=[CH:27][CH:28]=2)[CH3:33])=[O:9])=[CH:5][N:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 27611086-Cyanopyridine-3-carboxylic acidHCID 218916913-Cyclopropylmethyl-8-[4-(methylamino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydropurine-2,6-dione

Product 1

HCID 58739242HCID 58739242, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

This compound was prepared by a method similar to that described in example 79 except that 6-cyanonicotinic acid (Lancaster) was used in place of N-acetyl-6-amino-2-pyridine carboxylic acid, 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 0.68 equivalents of 4-dimethylaminopyridine was added as the final reagent to the reaction mixture. The product was purified by chromatography using silica gel eluted with 5:95 hexanes/ethyl acetate followed by crystallization from acetonitrile. MS, m/z(M+)=564.2161.

Workup

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

Sources & evidence

ORD record
ord-09308855ce774e998a824a1dcb0c356b
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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