Triethylamine → HCID 67406590, compound

HRID 1174290Notes

Reaction equation

HRID 1174290 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[N:5]=[C:6]([CH3:9])[S:7][CH:8]=1.[CH3:10][C@@H:11]([CH2:30][CH3:31])[C@H:12]([NH:17][C:18]([O:20]C1C=CC([N+]([O-])=O)=CC=1)=O)[C:13]([O:15][CH3:16])=[O:14].C(N(CC)CC)C>C1COCC1.CN(C1C=CN=CC=1)C>[CH3:10][C@@H:11]([CH2:30][CH3:31])[C@H:12]([NH:17][C:18]([N:2]([CH3:1])[CH2:3][C:4]1[N:5]=[C:6]([CH3:9])[S:7][CH:8]=1)=[O:20])[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 18939489N-Methyl-1-(2-methyl-1,3-thiazol-4-yl)methanamineHCID 69784564HCID 69784564, compound

Product 1

HCID 67406590HCID 67406590, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution containing the product from Example 109B (0.200 g, 1.4 mmol) in THF (6 mL) was treated with the product from Example 109C (0.415 g, 1.4 mmol), triethylamine (0.196 mL, 1.4 mmol), and DMAP (0.020 g, 0.16 mmol) at 25° C., stirred at reflux for 1 hour, cooled and concentrated. The residue was partitioned between ethyl acetate and 5% K2CO3. The organic phase was washed with brine and dried over Na2SO4, filtered and concentrated to give the title compound (0.38 mg, 86% yield).

Workup

  1. temperatureat reflux for 1 hour
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe residue was partitioned between ethyl acetate and 5% K2CO3
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7fd0dc2b86724f7caecfa41643ab798c
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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