4-Hydroxybenzoic Acid → 8-Chloro-1-{4-[5-(4-hydroxyphenyl)-1,2,4-oxadiazol-3-yl]butyl}-3-propyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1097687Notes

Reaction equation

HRID 1097687 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[Cl:11][C:12]1[NH:20][C:19]2[C:18](=[O:21])[N:17]([CH2:22][CH2:23][CH2:24][CH2:25]/[C:26](=[N:29]/[H])/[NH:27]O)[C:16](=[O:31])[N:15]([CH2:32][CH2:33][CH3:34])[C:14]=2[N:13]=1.ClC1NC2C(=O)N(CCCC/C(=N/[H])/NO)C(=O)N(CCCCC)C=2N=1>CS(C)=O>[Cl:11][C:12]1[NH:20][C:19]2[C:18](=[O:21])[N:17]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[N:27]=[C:6]([C:5]4[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=4)[O:8][N:29]=3)[C:16](=[O:31])[N:15]([CH2:32][CH2:33][CH3:34])[C:14]=2[N:13]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 178506471HCID 178506471, compoundHCID 178506473HCID 178506473, compound

Product 1

HCID 1361587918-Chloro-1-{4-[5-(4-hydroxyphenyl)-1,2,4-oxadiazol-3-yl]butyl}-3-propyl-3,7-dihydro-1H-purine-2,6-dioneYield 11%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

4-Hydroxybenzoic acid (18 mg, 0.13 mmol) and CDl (24 mg, 0.15 mmol) were stirred in anhydrous DMSO (0.9 ml) at rt for 1 h. (1Z)-5-(8-Chloro-2,6-dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxypentanimidamide (50 mg, 0.15 mmol; prepared in a manner similar to (1Z)-5-(8-Chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxypentanimidamide as described in Example 128(b)) was added and the mixture was stirred at 90° C. for 2 h. The reaction mixture was purified by MDAP. The product fraction was combined and concentrated under high vacuum to give the title compound as a white solid (7 mg, 11%).

Workup

  1. additionwas added
  2. customThe reaction mixture was purified by MDAP
  3. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-04c07c1a2d2447d7b506e5d9306ecc2b
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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