Hydrochloric Acid → HCID 24986175, compound

HRID 642986Notes

Reaction equation

HRID 642986 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]([CH3:28])[C:23](=[O:27])OCC)=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.[OH-].[Na+].Cl.ClC1SC(C(NCC2N=NN(C3C=CC(NC)=CC=3)C=2)=O)=CC=1.CCN(C(C)C)C(C)C.[CH3:64][O:65][CH2:66]C(Cl)=O>CS(C)=O.CO>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]([CH3:28])[C:23](=[O:27])[CH2:64][O:65][CH3:66])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 24986173HCID 24986173, compoundHCID 59260066HCID 59260066, compound

Product 1

HCID 24986175HCID 24986175, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

Compound 25 (60 mg, 0.14 mmol) was treated with 2 mL 2N NaOH and 2 mL methanol at 80° C. for 2 hrs and acidified with 2N HCl. The major product in this reaction, 5-chloro-N-((1-(4-(methylamino)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide, was isolated with prep HPLC. MS found for C15H14ClN5OS (M+H)+ 348.1, 350.1. This compound (10 mg, 0.023 mmol) was dissolved in 1 mL DMSO. To it were added 20 μL DIEA and CH3OCH2COCl (25 μL, 0.23 mmol). The mixture was stirred for 30 min and directly subjected to prep HPLC to isolate the title compound. MS found for C18H18ClN5O3S (M+H)+ 420.1, 422.1 (Cl pattern).

Workup

  1. customwas isolated with prep HPLC

Sources & evidence

ORD record
ord-d58c20d95062442f8a0471a89331a6c8
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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