Hydrochloric Acid → HCID 23503229, compound

HRID 1835140Notes

Reaction equation

HRID 1835140 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][N:10]1[C:15](=[O:16])[C:14]2[CH:17]=[CH:18][S:19][C:13]=2[C:12]([CH2:20][CH:21]([CH3:23])[CH3:22])=[N:11]1.O.Cl.[C:26]1([CH:36]=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1>O1CCCC1>[OH:37][CH:36]([C:18]1[S:19][C:13]2[C:12]([CH2:20][CH:21]([CH3:23])[CH3:22])=[N:11][N:10]([CH3:9])[C:15](=[O:16])[C:14]=2[CH:17]=1)[C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 61951-NaphthaldehydeHCID 2724682Lithium diisopropylamideHCID 22054401HCID 22054401, compound

Product 1

HCID 23503229HCID 23503229, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Lithium diisopropylamide (6.75 mmol) in tetrahydrofuran (8 ml) and 1-naphthaldehyde (0.7 ml) in tetrahydrofuran (5 ml) were added alternately to a solution of 5-methyl-7-(2-methylpropyl)thieno[2,3-d]pyridazin-4(5H)-one (1 g) prepared in b) above in tetrahydrofuran (20 ml) at 0° C. After 2 hours, water (10 ml) was added, the reaction mixture was acidified with dilute hydrochloric acid and then extracted with ethyl acetate. The organic phase was washed once with dilute hydrochloric acid, twice with saturated sodium hydrogen carbonate solution and once with brine, before being dried and evaporated. Purification by chromatography eluting with isohexane/ethyl acetate (1:1), and subsequent HPLC eluting with the same gave the title compound (0.4 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed once with dilute hydrochloric acid, twice with saturated sodium hydrogen carbonate solution and once with brine
  3. custombefore being dried
  4. customevaporated
  5. customPurification by chromatography
  6. washeluting with isohexane/ethyl acetate (1:1), and subsequent HPLC
  7. washeluting with the

Sources & evidence

ORD record
ord-6c2b8459d4ff445a84c013b517695cab
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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