Triethylamine hydrochloride → HCID 178521718, compound

HRID 1247507Notes

Reaction equation

HRID 1247507 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl.C(N(CC)CC)C.[Cl:13][C:14]1[S:38][C:17]2[NH:18][C:19]([C:21]([NH:23][CH:24]3[CH2:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH2:34][C:35]#[N:36])[C:25]3=[O:37])=[O:22])=[CH:20][C:16]=2[CH:15]=1>CN1CCCC1=O.CCOC(C)=O>[Cl:13][C:14]1[S:38][C:17]2[NH:18][C:19]([C:21]([NH:23][CH:24]3[CH2:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH2:34][C:35]4[NH:36][N:3]=[N:2][N:1]=4)[C:25]3=[O:37])=[O:22])=[CH:20][C:16]=2[CH:15]=1

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 104526402-Chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 178521718HCID 178521718, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

Sodium azide (178 mg, 2.73 mmol) and triethylamine hydrochloride (356 mg, 2.59 mmol) were added to 2-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 27; 300 mg, 0.78 mmol) in 1-methyl-2-pyrrolidinone (7 mL) and then heated at 150° C. for 3 hours. On cooling the mixture was diluted with EtOAc (100 mL) and washed with H2O (50 mL). The aqueous layer was acidified with citric acid and extracted with MeOH:DCM (1:19) and the combined organics dried (MgSO4), filtered and evaporated. The residue was purified by applying the material to a 10 g Isolute NH2 column in MeOH:DCM (1:9) (10 mL) and eluting with MeOH:DCM (1:9) (6×10 mL). The column was eluted with MeOH: 2M HCl in Et2O:DCM (5:4:45) (6×10 mL) and the relevant fractions evaporated to afford the title product (246 mg, 74%) as pale pink powder.

Workup

  1. temperatureOn cooling the mixture
  2. washwashed with H2O (50 mL)
  3. extractionextracted with MeOH:DCM (1:19)
  4. dry with materialthe combined organics dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified
  8. washeluting with MeOH:DCM (1:9) (6×10 mL)
  9. washThe column was eluted with MeOH
  10. custom2M HCl in Et2O:DCM (5:4:45) (6×10 mL) and the relevant fractions evaporated

Sources & evidence

ORD record
ord-b2084b9ba26a4069ab8ff703e546b893
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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