Hydrochloric Acid → 4-[(3-Chloro-4-fluorophenyl)amino]-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carbonitrile

HRID 38542Notes

Reaction equation

HRID 38542 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]3[S:18][C:19]4[CH2:20][N:21](C(OC(C)(C)C)=O)[CH2:22][CH2:23][C:24]=4[C:11]=23)[CH:5]=[CH:6][C:7]=1[F:8].Cl.O1CCOCC1>CC(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]3[S:18][C:19]4[CH2:20][NH:21][CH2:22][CH2:23][C:24]=4[C:11]=23)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58116801tert-Butyl 4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

Product 1

HCID 581169284-[(3-Chloro-4-fluorophenyl)amino]-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carbonitrileYield 105.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c′]dipyridine-7(6H)-carboxylate from Example 54A (250 mg, 0.365 mmol) was dissolved in 2-propanol (2 mL), and 4 M gaseous hydrogen chloride in dioxane (0.18 mL, 0.72 mmol) was added. The mixture was stirred at 80° C. for 1.5 h. The solvent was removed, and the residue was treated with 1 M aqueous sodium hydroxide solution (5 mL). The precipitate was collected by suction filtration, washed with water and dried in vacuo to yield 138 mg (99%) of the title compound.

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with 1 M aqueous sodium hydroxide solution (5 mL)
  3. filtrationThe precipitate was collected by suction filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-5f640e8c21184c98ae81ce3c6696a453
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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