Diethylamine → HCID 58033042, compound

HRID 533993Notes

Reaction equation

HRID 533993 reaction equation
Br[CH:2]([CH2:19][CH3:20])[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].[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22]>CN(C)C=O>[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]([N:23]([CH2:24][CH3:25])[CH2:21][CH3:22])[CH2:19][CH3:20])=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 58033007HCID 58033007, compound

Product 1

HCID 58033042HCID 58033042, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-N-[5-(2-chloro-benzyl)-thiazol-2-yl]-butyramide (37 mg, 0.10 mmol) was dissolved in 0.5 mL of N,N-dimethylformamide containing diethylamine (146 mg, 2.00 mmol). The reaction vessel was sealed and then subjected to microwave irradiation for 5 minutes at 80° C. The crude mixture was evaporated to dryness and purified by reverse-phase preparative liquid chromatography (14 mg, 0.038, 38%). ESI-MS m/z calc. 365.1. found 366.2 (M+1)+ Retention time 2.18 minutes.

Workup

  1. customThe reaction vessel was sealed
  2. customirradiation for 5 minutes at 80° C
  3. customThe crude mixture was evaporated to dryness
  4. custompurified by reverse-phase preparative liquid chromatography (14 mg, 0.038, 38%)

Sources & evidence

ORD record
ord-13a5e480686a476abfc540e01f7edcb3
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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