Hydrochloric Acid → HCID 58739237, compound

HRID 720613Notes

Reaction equation

HRID 720613 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([NH:14][C:15]2[C:16](=[O:56])[N:17]([CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[F:55])[C:18](=[O:47])[N:19]([CH2:22][C:23]3[N:27]=[CH:26][N:25]([C:28]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:24]=3)[C:20]=2[NH2:21])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>CO>[F:55][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=1[CH2:48][N:17]1[C:16](=[O:56])[C:15]2[NH:14][C:12]([CH2:11][C:8]3[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=3)=[N:21][C:20]=2[N:19]([CH2:22][C:23]2[N:27]=[CH:26][N:25]([C:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:24]=2)[C:18]1=[O:47]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58739260HCID 58739260, compound

Product 1

HCID 58739237HCID 58739237, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-(4-acetylamino-phenyl)-N-[6-amino-3-(2-fluoro-benzyl)-2,4-dioxo-1-(1-trityl-1H-[1,2,4]triazol-3-ylmethyl)-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide (50 mg, 0.06 mmol) in methanol (2.0 mL) was treated with a 10% aqueous sodium hydroxide solution (0.8 mL). The reaction was heated to 50° C. for 8 h. At this time, the reaction was cooled to 0° C., acidified with a 3N aqueous hydrochloric acid solution, filtered, and washed with water to afford N-{4-[1-(2-fluoro-benzyl)-2,6-dioxo-3-(1-trityl-1H-[1,2,4]triazol-3-ylmethyl)-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-acetamide (36 mg, 75%) as an off-white solid: 1H NMR (DMSO-d6, 300 MHz) δ13.45 (broad s, 1H), 9.87 (s, 1H), 7.94 (s, 1H), 7.47–6.89 (m, 23H), 5.21 (s, 2H), 5.07 (s, 2H), 3.95 (s, 2H), 2.48 (s, 3H).

Workup

  1. temperatureAt this time, the reaction was cooled to 0° C.
  2. filtrationfiltered
  3. washwashed with water

Sources & evidence

ORD record
ord-5857aa92b3424a008b135b35a3ebdf99
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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