Morpholine → HCID 58033018, compound

HRID 1771507Notes

Reaction equation

HRID 1771507 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].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>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:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 58033009HCID 58033009, compound

Product 1

HCID 58033018HCID 58033018, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-N-[5-(2-chloro-benzyl)-thiazol-2-yl]-2-phenyl-acetamide (42 mg, 0.10 mmol) was dissolved in 0.5 mL of N,N-dimethylformamide containing morpholine (174 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 (31 mg, 0.072, 72%). ESI-MS m/z calc. 427.1, found 428.0 (M+1)+ Retention time 2.40 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 (31 mg, 0.072, 72%)

Sources & evidence

ORD record
ord-7c207edbaad44a409e04ce719b120181
Source dataset
uspto-grants-2016_02
Patent number
US09249131B2

Reaction notes

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