Hydrochloride methanol → 1-(2-Methoxyl-5-chlorophenyl)-3-[1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1H-indol-4-yl]urea hydrochloride

HRID 240480Notes

Reaction equation

[O:1]([C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[NH:10][C:11]([NH:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[CH:17][N:18]2[CH2:23][C:24]1[C:32]2[C:27](=[N:28][CH:29]=[CH:30][CH:31]=2)[N:26](C(OC(C)(C)C)=O)[CH:25]=1)=[O:12])[CH3:2].CO.Cl>>[ClH:9].[O:1]([C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[NH:10][C:11]([NH:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[CH:17][N:18]2[CH2:23][C:24]1[C:32]2[C:27](=[N:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:12])[CH3:2]

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 687499901-(2-methoxyl-5-chlorophenyl)-3-{1-[1-(t-butyloxycarbonyl)-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl]-1H-indol-4-yl}urea

Product 1

HCID 687496781-(2-Methoxyl-5-chlorophenyl)-3-[1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1H-indol-4-yl]urea hydrochlorideYield 185.7%

Procedure

To 1-(2-methoxyl-5-chlorophenyl)-3-{1-[1-(t-butyloxycarbonyl)-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl]-1H-indol-4-yl}urea (500 mg, 0.92 mmol) was added hydrogen chloride methanol solution (25%), and the resulting mixture was stirred overnight, then concentrated to give the product 1-(2-Methoxyl-5-chlorophenyl)-3-[1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1H-indol-4-yl]urea hydrochloride (412 mg, 93%).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-795ba635c5d04cd78e872ec7023d0041
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648086B2

Reaction notes

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