Diethylamine → HCID 178464121, compound

HRID 1888258Notes

Reaction equation

HRID 1888258 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][N:12]=[C:11]3[CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:27][CH2:28][S:29](Cl)(=[O:31])=[O:30].[CH2:33]([N:35](CC)[CH2:36][CH3:37])[CH3:34].C([O-])([O-])=O.[K+].[K+].C(NCC)C>CN(C=O)C>[CH2:33]([N:35]([CH2:36][CH3:37])[CH2:27][CH2:28][S:29]([N:23]1[CH2:24][CH2:25][CH:20]([C:11]2[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)[CH:9]=3)[NH:13][N:12]=2)[CH2:21][CH2:22]1)(=[O:31])=[O:30])[CH3:34]

Participants

7

Reactant 5

HCID 8021DiethylamineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 1785135395-(3-fluorophenyl)-3-(4-piperidinyl)-1H-indazole-7-carboxamide2×

Product 1

HCID 178464121HCID 178464121, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure described in Example 33. Thus, 5-(3-fluorophenyl)-3-(4-piperidinyl)-1H-indazole-7-carboxamide (Intermediate 15) (75 mg, 0.167 mmol) was reacted with 2-chloro-1-ethanesulfonyl chloride (17 uL, 0.167 mmol) in the presence of triethyl amine (93 uL, 0.665 mmol) in DMF (2 mL) at 0° C. After 10 mins., K2CO3 (46 mg, 0.334 mmol) and diethyl amine (52 uL, 0.501 mmol) were added to afford the title compound (12.1 mg, 14% for 2 steps).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-64717019b6d14e1c83badc226647ace0
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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