Triethylamine → HCID 11988390, compound

HRID 1715298Notes

Reaction equation

HRID 1715298 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16](Cl)=[O:17])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].C([N:21](CC)CC)C>C1COCC1>[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16]([NH2:21])=[O:17])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86621993HCID 86621993, compound

Product 1

HCID 11988390HCID 11988390, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2′-Acetylamino-4′-methyl-[4,5′]bithiazolyl-2-carbonyl chloride, prepared as in Step I of Example 13, described above, (110 mg; 0.36 mmol; 1 eq.), is dissolved in anhydrous THF (10 ml). Under nitrogen, triethylamine (0.08 ml; 0.55 mmol; 1.5 eq) is added. Ammonia (gas) is bubbled during 10 minutes. The flask is closed and the reaction mixture is stirred for 20 additional minutes at RT. The solvents are removed and the crude product is directly purified by preparative HPLC, affording Compound (62) as a white-off solid (25.6 mg; 22%).

Workup

  1. customAmmonia (gas) is bubbled during 10 minutes
  2. customThe flask is closed
  3. customThe solvents are removed
  4. customthe crude product is directly purified by preparative HPLC

Sources & evidence

ORD record
ord-bbaeb8ebcb6a49868bbcdd1532e02539
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

Loading…