Methylamine → HCID 22143589, compound

HRID 985237Notes

Reaction equation

HRID 985237 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[C:14]([C:16]([OH:18])=O)[N:15]=3)[S:10][C:3]=12.C(Cl)(=O)C(Cl)=O.[CH3:25][NH2:26]>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[C:14]([C:16]([NH:26][CH3:25])=[O:18])[N:15]=3)[S:10][C:3]=12

Participants

6

Reactant 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 221435862-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazole-4-carboxylic acid

Product 1

HCID 22143589HCID 22143589, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent4×

Procedure

To a solution of 2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazole-4-carboxylic acid 43a (0.123 g, 0.41 mmole) in CH2Cl2 cooled at 0° C. was added 2.0 M oxalyl chloride in CH2Cl2 (0.520 ml, 1.04 mmole) and DMF (2 drops). The reaction mixture was stirred at room temperature for 1 h, concentrated and dried. The residue was taken into CH2Cl2 (10 ml), and 2.0 M methylamine in CH2Cl2 (0.250 ml, 0.492 mmole) was added. The reaction mixture was stirred at room temperature for 1 h, and then partitioned between H2O (100 ml) and CH2Cl2 (2×100 ml). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 2-8% CH3OH in CH2Cl2 to give yellow solid (0.116 g, 91%). 1H NMR (300 MHz, CDCl3) δ8.62 (1H, d, J=5.1 Hz), 8.19 (1H, s), 7.96 (1H, s), 7.33 (1H, d, J=5.1 Hz), 3.06 (3H, d, J=4.9 Hz); ESIMS (MH+): 309.95.

Workup

  1. concentrationconcentrated
  2. customdried
  3. additionwas added
  4. stirringThe reaction mixture was stirred at room temperature for 1 h
  5. custompartitioned between H2O (100 ml) and CH2Cl2 (2×100 ml)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography
  9. washeluting with 2-8% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-5ae6231f6cd64043940c16135097990a
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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