Methylamine → HCID 58033039, compound

HRID 533987Notes

Reaction equation

HRID 533987 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][NH2:26]>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]([NH:26][CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 58033009HCID 58033009, compound

Product 1

HCID 58033039HCID 58033039, 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 1.0 mL of methylamine (2.0 M in tetrahydrofuran, 2.0 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, dissolved in 1 mL of dimethylsulfoxide and purified by reverse-phase preparative liquid chromatography (29 mg, 0.078, 78%). ESI-MS m/z calc. 371.1. found 372.2 (M+1)+ Retention time 2.33 minutes. 1H NMR (400 MHz, MeOD) δ 2.66 (s, 3H), 4.23 (s, 2H), 5.09 (s, 1H), 7.13-7.56 (m, 10H).

Workup

  1. customThe reaction vessel was sealed
  2. customirradiation for 5 minutes at 80° C
  3. customThe crude mixture was evaporated to dryness
  4. dissolutiondissolved in 1 mL of dimethylsulfoxide
  5. custompurified by reverse-phase preparative liquid chromatography (29 mg, 0.078, 78%)

Sources & evidence

ORD record
ord-a3a0ed18752f4ed1aad012341dbd7f98
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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