Potassium Carbonate → 5-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

HRID 2267495Notes

Reaction equation

[NH2:1]S(N)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](C(N)=O)=[C:10]2[CH:19]1[CH2:24][CH2:23][N:22]([S:25]([CH2:28][CH2:29][CH2:30]Cl)(=[O:27])=[O:26])[CH2:21][CH2:20]1.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.[C:37]([O-:40])([O-])=O.[K+].[K+]>>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([C:37]([NH2:1])=[O:40])[CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:19]1[CH2:20][CH2:21][N:22]([S:25]([CH2:28][CH2:29][CH2:30][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)(=[O:27])=[O:26])[CH2:23][CH2:24]1

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 31268Pyrrolidine

HCID 82267Sulfamide

HCID 687912945-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indole-carboxamide

Product 1

HCID 590033005-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamideYield 87%

Procedure

Following the general procedure for aminosulfonamide formation outlined in example 2, 5-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indole-carboxamide (656 mg, 1.41 mmol) and pyrrolidine (505 mg, 7.05 mmol) were allowed to react in the presence of K2CO3 (389.16 mg, 2.82 mmol). The resulting residue was purified by reverse phase HPLC eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to give the title compound (600 mg, 87%).

Workup

customThe resulting residue was purified by reverse phase HPLC
washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-b8811802518042b1ae5e4a15f9a8935b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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