Isobutanol → (S)-N-{1-[4-(2'-Isobutoxy-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)-phenyl]-ethyl}-acetamide

HRID 1470760Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][C:23](=[O:25])[CH3:24])[CH3:21])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[CH2:26]([OH:30])[CH:27]([CH3:29])[CH3:28].[H-].[Na+]>O1CCOCC1>[CH2:26]([O:30][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][C:23](=[O:25])[CH3:24])[CH3:21])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1)[CH:27]([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 130 °C

Procedure

To a mixture of 34 mg (0.10 mmol) (S)—N-{1-[4-(2′-fluoro-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-4-yl)-phenyl]-ethyl}-acetamide (XIX.1) and 74 mg (1.0 mmol) isobutyl alcohol in 2 mL dioxane is added 20 mg (0.50 mmol) NaH (60% in mineral oil). The mixture is stirred at 130° C. for 12 h. The solvent is removed in vacuo and the residue is purified by HPLC (RP X-Bridge; water (+0.1% TFA)/MeOH) to yield the desired product.

Workup

customThe solvent is removed in vacuo
customthe residue is purified by HPLC (RP X-Bridge; water (+0.1% TFA)/MeOH)

Sources & evidence

ORD record: ord-e8389fea41d0405d9266c78e3b45f0f9
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006450B2

Reaction notes

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