1-Methoxybutan-2-yl 4-methylbenzene-1-sulfonate → 4-(1-((2S)-1-methoxybutan-2-yl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

HRID 2206217Notes

Reaction equation

HRID 2206217 reaction equation
C[O:2][C:3]1[C:8]2[C:9]([C:12]3[CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[S:15][CH:16]=3)=[N:10][NH:11][C:7]=2[CH:6]=[CH:5][N:4]=1.CC1C=CC(S(O[CH:31]([CH2:35][CH3:36])[CH2:32][O:33][CH3:34])(=O)=O)=CC=1>O.C(#N)C>[CH3:34][O:33][CH2:32][C@@H:31]([N:11]1[C:7]2[CH:6]=[CH:5][NH:4][C:3](=[O:2])[C:8]=2[C:9]([C:12]2[CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[S:15][CH:16]=2)=[N:10]1)[CH2:35][CH3:36]

Participants

4

Reactant 2

HCID 127007761-Methoxybutan-2-yl 4-methylbenzene-1-sulfonateHCID 1179879184-(4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-Thiophenecarboxamide

Product 1

HCID 1370106294-(1-((2S)-1-methoxybutan-2-yl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The racemic form of the title compound was obtained using 4-(4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide obtained in Step A of Example 148 and 1-methoxybutan-2-yl 4-methylbenzenesulfonate, in the same manner as in Step B of Example 148 and Step C of Example 148. The obtained racemic form was resolved by HPLC (column: L-column2 ODS (trade name) 20 mmID×150 mmL, 5 μm, manufactured by Daicel Chemical Industries, mobile phase: water/acetonitrile (containing 10 mM ammonium carbonate)) to give the title compound having a shorter retention time.

Sources & evidence

ORD record
ord-22572f7a8b4940e0a7c18c9e0690e5e3
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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