Hydrochloric Acid → HCID 86651629, compound

HRID 57712Notes

Reaction equation

HRID 57712 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH:9][CH2:10][CH2:11][NH:12][C:13]2[C:14]3[N:15]([N:27]=[C:28]([C:30](OCC)=[O:31])[CH:29]=3)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[N:18]=2)[S:5][C:6]=1[C:7]#[N:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.Cl>C1COCC1>[NH2:1][C:2]1[N:3]=[C:4]([NH:9][CH2:10][CH2:11][NH:12][C:13]2[C:14]3[N:15]([N:27]=[C:28]([CH2:30][OH:31])[CH:29]=3)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[N:18]=2)[S:5][C:6]=1[C:7]#[N:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21226445Aluminium lithium hydrideHCID 86651630HCID 86651630, compound

Product 1

HCID 86651629HCID 86651629, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

100 mg (0.184 mmol) of ethyl 4-({2-[(4-amino-5-cyano-1,3-thiazol-2-yl)amino]ethyl}amino)-6-(2,4-dichlorophenyl)pyrazolo[1,5-a]pyrazine-2-carboxylate (Example 11) were dissolved in 10 ml of THF, and 0.276 ml (0.276 mmol) of a solution of lithium aluminum hydride (1 mol/l) in THF was added dropwise at RT. The mixture was stirred for 2 h, and after complete conversion first methanol was added, and then the pH was adjusted to pH=5 using dilute hydrochloric acid. The mixture was extracted repeatedly with ethyl acetate. Removal of the solvent and purification by preparative HPLC gave 61 mg (64% of theory) of the product as a solid.

Workup

  1. extractionThe mixture was extracted repeatedly with ethyl acetate
  2. customRemoval of the solvent and purification by preparative HPLC

Sources & evidence

ORD record
ord-d3550c77304743bcb3a4627806826460
Source dataset
uspto-grants-2016_09
Patent number
US09434731B2

Reaction notes

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