Hydrochloric Acid → 4-(5-(1-oxoisoindolin-5-yl)imidazo[1,2-a]pyridin-8-ylamino)-N-(pyrrolidin-3-yl)benzene sulfonamide

HRID 552393Notes

Reaction equation

HRID 552393 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[C:25]4[N:26]([CH:40]=[CH:41][N:42]=4)[C:27]([C:30]4[CH:31]=[C:32]5[C:36](=[CH:37][CH:38]=4)[C:35](=[O:39])[NH:34][CH2:33]5)=[CH:28][CH:29]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:9]1)=O)(C)(C)C.ClC1N2C=CN=C2C(NC2C=CC(N3CCN(C(C)C)CC3)=CC=2)=CC=1.Cl>O1CCOCC1>[O:39]=[C:35]1[C:36]2[C:32](=[CH:31][C:30]([C:27]3[N:26]4[CH:40]=[CH:41][N:42]=[C:25]4[C:24]([NH:23][C:20]4[CH:19]=[CH:18][C:17]([S:14]([NH:13][CH:10]5[CH2:11][CH2:12][NH:8][CH2:9]5)(=[O:15])=[O:16])=[CH:22][CH:21]=4)=[CH:29][CH:28]=3)=[CH:38][CH:37]=2)[CH2:33][NH:34]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 57580808(5-Chloro-imidazo[1,2-a]pyridin-8-yl)-[4-(4-isopropyl-piperazin-1-yl)-phenyl]-amineHCID 671207883-{4-[5-(1-Oxo-2,3-dihydro-1H-isoindol-5-yl)-imidazo[1,2-a]pyridin-8-ylamino]-benzenesulfonylamino}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 249888924-(5-(1-oxoisoindolin-5-yl)imidazo[1,2-a]pyridin-8-ylamino)-N-(pyrrolidin-3-yl)benzene sulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-{4-[5-(1-oxo-2,3-dihydro-1H-isoindol-5-yl)-imidazo[1,2-a]pyridin-8-ylamino]-benzenesulfonylamino}-pyrrolidine-1-carboxylic acid tert-butyl ester (16 mg, 0.027 mmol), prepared using methods as described for compound 12, is suspended in a 4M solution of HCl in dioxane (0.5 mL) and the mixture is stirred under nitrogen at room temperature for 16 hours. The mixture is concentrated under reduced pressure. The crude product is purified by reverse phase HPLC to yield the title compound.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customThe crude product is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-93480252c9c948a5af382cae36f02c91
Source dataset
uspto-grants-2011_05
Patent number
US07951818B2

Reaction notes

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