Cyclopentylamine → HCID 178513549, compound

HRID 1888259Notes

Reaction equation

HRID 1888259 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].C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+].[CH:46]1([NH2:51])[CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C=O)C>[CH:46]1([NH:51][CH2:27][CH2:28][S:29]([N:23]2[CH2:24][CH2:25][CH:20]([C:11]3[C:10]4[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=[C:8]([C:4]5[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=5)[CH:9]=4)[NH:13][N:12]=3)[CH2:21][CH2:22]2)(=[O:31])=[O:30])[CH2:50][CH2:49][CH2:48][CH2:47]1

Participants

7

Reactant 5

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 1785135395-(3-fluorophenyl)-3-(4-piperidinyl)-1H-indazole-7-carboxamide2×

Product 1

HCID 178513549HCID 178513549, compoundYield 8.1%

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 cyclopentyl amine (49 uL, 0.501 mmol) were added to afford the title compound (4.9 mg, 8.1% for 2 steps).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-b62eaab1db174b94b6b7428f361bdc93
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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