Phenol → 8-(3-Aminoazepan-1-yl)-7-benzyl-1,3-dimethyl-3,7-dihydropurine-2,6-dione

HRID 984818

反応式

HRID 984818 の反応式
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]([CH3:20])[C:11]=2[N:10]=[C:9]1[N:21]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]([NH:28]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(O)C=CC=CC=1.CCOC(C)=O>Br.C1C=CC=CC=1>[NH2:28][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][N:21]([C:9]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]3[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]([CH3:20])[C:11]=3[N:10]=2)[CH2:22]1

参加物

6

反応物 3

HCID 996PhenolHCID 8857Ethyl AcetateHCID 22508573N-(1-(7-Benzyl-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-8-yl)azepan-3-yl)-4-methylbenzenesulfonamide

生成物 1

HCID 101345098-(3-Aminoazepan-1-yl)-7-benzyl-1,3-dimethyl-3,7-dihydropurine-2,6-dione

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 260Hydrogen Bromide溶媒

実験手順

N-(1-(7-Benzyl-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-8-yl)azepan-3-yl)-4-methylbenzenesulfonamide (6C) (100 mg, 0.19 mmol) was dissolved in hydrobromic acid (48%, 5 ml) and benzene (0.07 ml), and phenol (61.4 mg, 0.65 mmol) was added. The mixture was heated to reflux for three hours, and after cooling 20 ml of EtOAc was added. The layers were separated, and the aqueous layer washed with 20 ml of EtOAc. pH was adjusted to 11 with 10M sodium hydroxide. The aqueous layer was extracted with diethyl ether (3×20 ml), and the combined organic layers were dried over sodium sulphate and the solvent was evaporated. The crude product was dissolved in 5 ml of DCM and 0.5 ml of trifluoroacetic acid was added. The solvents were evaporated and the crude product was purified by preparative HPLC (method A1, Rt=7.63 min). Evaporation of the solvent gave the title compound as an oil.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for three hours
  3. additionwas added
  4. customThe layers were separated
  5. washthe aqueous layer washed with 20 ml of EtOAc
  6. extractionThe aqueous layer was extracted with diethyl ether (3×20 ml)
  7. dry with materialthe combined organic layers were dried over sodium sulphate
  8. customthe solvent was evaporated
  9. dissolutionThe crude product was dissolved in 5 ml of DCM
  10. addition0.5 ml of trifluoroacetic acid was added
  11. customThe solvents were evaporated
  12. customthe crude product was purified by preparative HPLC (method A1, Rt=7.63 min)
  13. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-daa9c3ca060c420fbe25ca700d3b5cdb
出典データセット
uspto-grants-2005_03
特許番号
US06869947B2

関連ノート

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