Triethylamine → HCID 11990230, compound

HRID 1715294Notes

Reaction equation

HRID 1715294 reaction equation
Br.Br[CH2:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)=[N:8][C:7]=1[CH3:18])=O.C(N(CC)CC)C.[C:26]([CH2:28][C:29]([NH2:31])=[S:30])#[N:27]>CCO>[CH3:18][C:7]1[N:8]=[C:9]([NH:11][C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)[S:10][C:6]=1[C:4]1[N:31]=[C:29]([CH2:28][C:26]#[N:27])[S:30][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14162772-CyanoethanethioamideHCID 131728330HCID 131728330, compound

Product 1

HCID 11990230HCID 11990230, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo- 1-[4-methyl-2-(pyrazin-2-ylamino)-1,3 -thiazol-5-yl]lethanone, (Intermediate 3) (75 mg; 0.19 mmol; 1 eq.) in EtOH (2 ml), is added triethylamine (66 μl; 0.48 mmol; 2.50 eq.) and 2-cyanothioacetamide (19.0 mg; 0.19 mmol; 1 eq.). The mixture is stirred overnight at rt. The reaction mixture is filtered and rinsed -with ethanol affording Compound (53) as brown solid (35.4 mg; 59%). 1H NMR (DMSO-d6) δ2.49 (s, 3H), 4.62 (s, 2H), 7.67 (s, 1H), 8.13 (m, 1H), 8.36 (m, 1H), 8.44 (m, 1H), 11.79 (br s, 1H). M31 (ESI): 312.88; M+(ESI): 314.95. HPLC (method A), Rt: 2.47 min (purity: 93.5%).

Workup

  1. filtrationThe reaction mixture is filtered
  2. washrinsed -with ethanol affording Compound (53) as brown solid (35.4 mg; 59%)

Sources & evidence

ORD record
ord-259b8f2667614cf5b36c1c24dea78575
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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