2-(hexamethyleneimino)ethyl chloride HCl → 5-[4-(2-Azepin-1-yl-ethylamino)-phenoxy]-6-(4-methanesulfonyl-phenyl)-naphthalen-2-ol Dihydrochloride

HRID 732787Notes

Reaction equation

HRID 732787 reaction equation
C(O[C:6](=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25]C)=[CH:22][CH:23]=3)[CH:18]=[CH:17][C:16]=2[C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[CH:10][CH:9]=1)(C)(C)C.[ClH:38].[N:39](=[CH:47]CCl)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][Cl:46]>>[ClH:46].[ClH:38].[N:39]1([CH2:47][CH2:6][NH:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][C:15]3[C:16]([C:27]4[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:31][CH:32]=4)=[CH:17][CH:18]=[C:19]4[C:24]=3[CH:23]=[CH:22][C:21]([OH:25])=[CH:20]4)=[CH:12][CH:13]=2)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=[CH:45]1

Participants

3

Reactant 2

HCID 534452772-(hexamethyleneimino)ethyl chloride HClHCID 68519035{4-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 685212905-[4-(2-Azepin-1-yl-ethylamino)-phenoxy]-6-(4-methanesulfonyl-phenyl)-naphthalen-2-ol DihydrochlorideYield 37%

Procedure

Using procedures similar to Preparation 18 and Example 58, convert {4-[2-(4-methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenyl}-carbamic acid tert-butyl ester (200 mg, 0.39 mmol) and 2-(hexamethyleneimino)-ethyl chloride hydrochloride (140 mg, 0.70 mmol) to 77 mg of the title compound (37%). Mass spectrum (ion spray): m/z=531 (M+H).

Workup

  1. customsimilar to Preparation 18 and Example 58

Sources & evidence

ORD record
ord-2321d48e60f3407a87190d465b5e3845
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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