2-Bromo-1,3-thiazole-5-carbonitrile → HCID 68580052, compound

HRID 2234049Notes

Reaction equation

HRID 2234049 reaction equation
Cl.[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11].Br[C:20]1[S:21][C:22]([C:25]#[N:26])=[CH:23][N:24]=1>CN1C(=O)CCC1.CCOC(C)=O>[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:20]2[S:21][C:22]([C:25]#[N:26])=[CH:23][N:24]=2)[CH2:15][CH2:14]1)=[O:11]

Participants

5

Reactant 2

HCID 178609522-Bromo-1,3-thiazole-5-carbonitrileHCID 68579996HCID 68579996, compound2×

Product 1

HCID 68580052HCID 68580052, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 3,4-dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1; 0.330 g, 1.058 mmol) in NMP (2 ml) was added TEA (0.150 ml, 1.058 mmol) followed by the addition of 2-bromo-1,3-thiazole-5-carbonitrile (prepared according to F. Campagna et al. Tet. Lett, 1977, 21, 1815-1816) (0.200 g, 1.058 mmol) at room temperature. Using a Smith Microwave Synthesizer, the mixture was subjected to single-mode microwave at 150° C. for 20 minutes. The crude mixture was diluted with EtOAc and washed with water several times. The extracts were combined dried over magnesium sulfate and concentrated to give the desired product. (0.450 g).

Workup

  1. customat 150° C.
  2. customfor 20 minutes
  3. washwashed with water several times
  4. dry with materialThe extracts were combined dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6a987e3030e84b81a1ff67f8793c1b32
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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