Aniline → HCID 58033121, compound

HRID 1771509Notes

Reaction equation

HRID 1771509 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].N[C:22]1[CH:27]=[CH:26][CH:25]=CC=1.[CH3:28][N:29](C)[CH:30]=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:29]([CH3:30])[CH3:28])[C:19]2[CH:20]=[CH:25][CH:26]=[CH:27][CH:22]=2)=[N:10][CH:9]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 6228DimethylformamideHCID 58033007HCID 58033007, compound

Product 1

HCID 58033121HCID 58033121, compound

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 aniline (186 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 (24 mg, 0.062, 62%). ESI-MS m/z calc. 385.1, found 386.1 (M+1)+ Retention time 3.48 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 (24 mg, 0.062, 62%)

Sources & evidence

ORD record
ord-b87b6495825d4463b16aabc73b1fdb96
Source dataset
uspto-grants-2016_02
Patent number
US09249131B2

Reaction notes

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