Sodium Iodide → 3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indazole-7-carboxamide

HRID 1888275Notes

Reaction equation

HRID 1888275 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:28]([NH2:30])=[O:29])[CH:19]=[C:20]([C:23]4[CH:27]=[CH:26][S:25][CH:24]=4)[CH:21]=3)[NH:16][N:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].C([O-])([O-])=O.[K+].[K+].[I-].[Na+].[NH:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>CN(C=O)C>[N:39]1([CH2:2][CH2:3][CH2:4][S:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[C:22]4[C:17](=[C:18]([C:28]([NH2:30])=[O:29])[CH:19]=[C:20]([C:23]5[CH:27]=[CH:26][S:25][CH:24]=5)[CH:21]=4)[NH:16][N:15]=3)[CH2:10][CH2:9]2)(=[O:7])=[O:6])[CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 178513564HCID 178513564, compound

Product 1

HCID 1785135653-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indazole-7-carboxamideYield 37.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure of Example 38b. Thus, 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indazole-7-carboxamide (0.076 mmol) in DMF (4 mL) was reacted with K2CO3 (22 mg, 0.16 mmol), sodium iodide (2 mg) and pyrrolidine (26.98 mL, 0.4 mmol) to afford the title compound (14.2 mg, 37%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-67260994912d45679d0f8dca9ad89c1a
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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