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

HRID 1888279Notes

Reaction equation

HRID 1888279 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+].C(N(CC)CC)C.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>CN(C=O)C>[N:44]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])[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 178513564HCID 178513564, compound

Product 1

HCID 1785135663-(1-{[3-(4-morpholinyl)propyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indazole-7-carboxamideYield 8.9%

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) (0.05 mmol) in DMF (2 mL) was reacted with K2CO3 (14 mg, 0.1 mmol), triethyl amine (42 uL, 0.3 mmol) and morpholine (22 uL, 0.25 mmol) to afford the title compound (2.3 mg, 8.8%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-c1a4e89974a045eb8ace9e0213673bad
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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