Hydrochloric Acid → 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid {4-[3-butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide

HRID 720636Notes

Reaction equation

HRID 720636 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[C:6](=[O:12])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[C:4](=[O:21])[C:3]=1[NH:22][C:23]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]2[N:39]=[CH:38][N:37]([C:40]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:36]=2)=[O:34])=[CH:28][CH:27]=1)=O.[OH-].[Na+].Cl>CO>[CH2:8]([N:7]1[C:2]2[N:1]=[C:23]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([NH:32][C:33]([C:35]4[N:39]=[CH:38][N:37]([C:40]([C:53]5[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=5)([C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=5)[C:41]5[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=5)[N:36]=4)=[O:34])=[CH:30][CH:31]=3)[NH:22][C:3]=2[C:4](=[O:21])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[C:6]1=[O:12])[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 587392261-trityl-1H-[1,2,4]triazole-3-carboxylic acid (4-{[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-amide

Product 1

HCID 587392251-trityl-1H-[1,2,4]triazole-3-carboxylic acid {4-[3-butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amideYield 60.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid (4-{[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-amide (70 mg, 0.09 mmol) in methanol (3.0 mL) heated to 50° C. was treated with a 10% aqueous sodium hydroxide solution (1.08 mL). The reaction was heated at 50° C. for 4 h. At this time, the reaction was treated with a 3N aqueous hydrochloric acid solution (0.9 mL). This solution was stirred at 25° C. for 30 min. The resulting solids were collected by filtration, washed with water, and dried in vacuo to afford 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid {4-[3-butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide (41.3 mg, 60.5%) as a pale yellow solid: EI-HRMS m/e calcd for C45H39N8O3F (M+Na)+781.3027, found 781.3039.

Workup

  1. filtrationThe resulting solids were collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-f70597494cc340ad95f7771c8ba75647
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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