Hydrochloric Acid → HCID 22250074, compound

HRID 889897Notes

Reaction equation

HRID 889897 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[S:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[Cl:20])[CH:12]=2)=[N:8][C:7]=1[CH3:21])=[O:5])C.C1COCC1.[OH-].[K+].Cl>C(O)C>[Cl:20][C:17]1[CH:16]=[CH:15][N:14]=[C:13]2[CH:12]=[C:11]([C:9]3[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH3:21])[N:8]=3)[S:19][C:18]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 69585794HCID 69585794, compound

Product 1

HCID 22250074HCID 22250074, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 15.2 g (46.2 mmol) 2-(7-chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carboxylic acid ethyl ester, 80 mL of THF and 20 mL of absolute ethanol was added (13 g, 231 mmol) freshly ground potassium hydroxide. The reaction was stirred at room temperature for sixteen hours. The reaction was cooled to 0° C. and the pH was adjusted to pH 3 with conc HCl. The resulting yellow precipitate was filtered and dried to give 2-(7-chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carboxylic acid (10.3 g) in 72% yield. C12H7N2O2S2: APCI m/z 310.2/312.2 (pos.); 1H NMR (d6-DMSO): δ 8.67 (d, 1H, J=5.0 Hz), 8.42 (s, 1H), 7.65 (d, 1H, J=5.0 Hz), 2.65 (s, 3H) ppm.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. filtrationThe resulting yellow precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-90d8a049298243a8bf7f56903cba1de3
Source dataset
uspto-grants-2006_02
Patent number
US06995171B2

Reaction notes

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