Hydrochloric Acid → HCID 77174803, compound

HRID 1008957Notes

Reaction equation

HRID 1008957 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[C:14]([NH:16][CH2:17][CH2:18][CH:19](OCC)[O:20]CC)[N:13]=[C:12]2[CH:26]=[CH:27][S:28][C:11]=12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:29]>C1COCC1>[ClH:29].[C:1]([O:9][C:10]1[CH:15]=[C:14]([NH:16][CH2:17][CH2:18][CH:19]=[O:20])[N:13]=[C:12]2[CH:26]=[CH:27][S:28][C:11]=12)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67304364HCID 67304364, compound

Product 1

HCID 77174803HCID 77174803, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude 5-(3,3-diethoxypropylamino)thieno[3,2-b]pyridin-7-yl benzoate from above (677.3 g, 1.68 mol) was dissolved in 3.0 L of THF. Then, 12N HCl (1.68 mol, 0.14 L) was added dropwise while the reaction temperature was maintained below 20° C. with an ice-water bath. After stirring for 5 minutes, solids precipitated. The resultant mixture was stirred at room temperature for 1 h, followed by the addition of ethyl acetate (2.0 L). The mixture was stirred for 30 min. The solids were filtered, rinsed with ethyl acetate (250 ml×2), and then dried under reduced pressure at 55° C. to give the title compound 5-(3-oxopropylamino)thieno[3,2-b]pyridin-7-yl benzoate HCl salt as a light brown solid. 1H NMR (400 MHz, DMSO d6) δ 2.20 (m, 2H), 3.56 (m, 2H), 6.31 (t, 1H, J=3.6 NHz), 7.83-7.87 (m, 2H), 7.96 (d, 1H, J=6.0 Hz), 8.16-8.20 (m, 2H), 8.35 (d, 1H, J=5.6 Hz), 10.20 (s, 1H).

Workup

  1. temperaturewas maintained below 20° C. with an ice-water bath
  2. customsolids precipitated
  3. stirringThe resultant mixture was stirred at room temperature for 1 h
  4. additionfollowed by the addition of ethyl acetate (2.0 L)
  5. stirringThe mixture was stirred for 30 min
  6. filtrationThe solids were filtered
  7. washrinsed with ethyl acetate (250 ml×2)
  8. customdried under reduced pressure at 55° C.

Sources & evidence

ORD record
ord-d3383282bd0d43cbba1d496a1dbc11a3
Source dataset
uspto-grants-2011_07
Patent number
US07973050B2

Reaction notes

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