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

HRID 1888276Notes

Reaction equation

HRID 1888276 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+].[CH3:39][NH:40][CH3:41]>CN(C=O)C>[CH3:39][N:40]([CH3:41])[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]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 178513564HCID 178513564, compound

Product 1

HCID 1784836153-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indazole-7-carboxamideYield 47%

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 (Example 48a) (0.076 mmol) in DMF (4 mL) was reacted with K2CO3 (22 mg, 0.16 mmol), sodium iodide (2 mg) and dimethyl amine (0.2 mL, 0.4 mmol) to afford the title compound (16.9 mg, 47%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-93b7beb2555846dd9c1d8cf3f82b1647
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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