Hydroxyamine hydrochloride → 2-(4-Cylopentyloxy-6-methyl-5-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridin-2-yl)-6-fluoro-phenyl-propan-1-one oxime

HRID 1392688Notes

Reaction equation

Cl.[NH2:2][OH:3].[CH:4]1([O:9][C:10]2[C:15]([CH2:16][N:17]([CH3:28])[CH:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[C:14]([CH3:29])[N:13]=[C:12]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=3[C:37](=O)[CH2:38][CH3:39])[CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5]1>N1C=CC=CC=1>[CH:4]1([O:9][C:10]2[C:15]([CH2:16][N:17]([CH3:28])[CH:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[C:14]([CH3:29])[N:13]=[C:12]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=3[C:37](=[N:2][OH:3])[CH2:38][CH3:39])[CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

Conditions

Temperature: 70 °C

Procedure

Hydroxylamine hydrochloride (47 mg, 0.7 mmol) is added to a solution of 1-[2-(4-cylopentyloxy-6-methyl-5-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridin-2-yl)-6-fluoro-pheny]-propan-1-one (151 mg, 0.3 mmol) in pyridine at room temperature. The mixture is heated to 70° C. for 16 hours. Solvent is removed in vacuo and the crude product is purified by PTLC eluting with 2% MeOH in DCM to give the title product.

Workup

customSolvent is removed in vacuo
customthe crude product is purified by PTLC
washeluting with 2% MeOH in DCM

Sources & evidence

ORD record: ord-441956a10de846069aaf615a2b2c722b
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342115B2

Reaction notes

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