Hydrochloric Acid → HCID 58997596, compound

HRID 1592071Notes

Reaction equation

HRID 1592071 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([N:14]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]3)=[CH:8][C:9]=2[CH2:11][CH2:12][CH3:13])[S:4][C:3]=1[C:21]#[N:22].[N:23](OCCC(C)C)=O.[ClH:31]>CCO>[Cl:31][C:21]1[C:3]2[S:4][C:5]3[N:6]=[C:7]([N:14]4[CH2:15][CH2:16][CH:17]([OH:20])[CH2:18][CH2:19]4)[CH:8]=[C:9]([CH2:11][CH2:12][CH3:13])[C:10]=3[C:2]=2[N:1]=[N:23][N:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 58997600HCID 58997600, compound

Product 1

HCID 58997596HCID 58997596, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Amino-6-(4-hydroxy-piperidin-1-yl)-4-propyl-thieno[2,3-b]pyridine-2-carbonitrile (316 mg, 1.00 mmol) (see Example 2) was dissolved in 3 mL of HCl in EtOH (1.25 M). To this solution at 0° C. was added isoamyl nitrite (0.42 mL, 3.0 mmol). The reaction mixture was warmed up to room temperature in 2 h. The resulting precipitate was collected by filtration and washed with MeOH to give 1-(4-chloro-9-propyl-pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]triazin-7-yl)-piperidin-4-ol as a yellow solid (120 mg, 35%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with MeOH

Sources & evidence

ORD record
ord-62e04b10b17e4a879e4f5d063cab688c
Source dataset
uspto-grants-2007_11
Patent number
US07291733B2

Reaction notes

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