Methanol → HCID 58032986, compound

HRID 533986Notes

Reaction equation

HRID 533986 reaction equation
Br[CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]([NH:5][C:6]1[S:7][C:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:9][N:10]=1)=[O:4].[CH3:25][OH:26]>>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][C:8]1[S:7][C:6]([NH:5][C:3](=[O:4])[CH:2]([O:26][CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:10][CH:9]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 58033009HCID 58033009, compound

Product 1

HCID 58032986HCID 58032986, compound

Procedure

2-Bromo-N-[5-(2-chloro-benzyl)-thiazol-2-yl]-2-phenyl-acetamide (42 mg, 0.10 mmol) was dissolved in 5 mL of methanol. The reaction vessel was sealed and then subjected to microwave irradiation for 15 minutes at 125° C. The crude mixture was evaporated to dryness, dissolved in 1 mL of dimethylsulfoxide and purified by reverse-phase preparative liquid chromatography (16 mg, 0.043, 43%). ESI-MS m/z calc. 372.1. found 373.2 (M+1)+ Retention time 3.43 minutes. 1H NMR (400 MHz, CD3CN) δ 3.42 (s, 3H), 4.23 (s, 2H), 4.94 (s, 1H), 7.21-7.53 (m, 10H)

Workup

  1. customThe reaction vessel was sealed
  2. customirradiation for 15 minutes at 125° C
  3. customThe crude mixture was evaporated to dryness
  4. dissolutiondissolved in 1 mL of dimethylsulfoxide
  5. custompurified by reverse-phase preparative liquid chromatography (16 mg, 0.043, 43%)

Sources & evidence

ORD record
ord-81ffaea8a9d646a1bbc52458c885d12f
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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