4-Hydroxybenzylamine → N-(3-Amino-propyl)-N-{3-[2-(4-hydroxy-benzylamino)-pyrimidin-4-yl]-benzyl}-methanesulfonamide

HRID 14709

Reaction equation

C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25](Cl)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:14])=[O:13])(C)(C)C.[NH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1>>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=3)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:13])=[O:14]

Participants

Reactant 2

HCID 974724-Hydroxybenzylamine

HCID 86603242(3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 58603579N-(3-Amino-propyl)-N-{3-[2-(4-hydroxy-benzylamino)-pyrimidin-4-yl]-benzyl}-methanesulfonamide

Procedure

Intermediate 4 from above was coupled with 4-aminomethyl-phenol following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 442.

Sources & evidence

ORD record: ord-8bb62e73a0bc4ceb817b3ba09e0e0e43
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Linked notes

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