4-Ethynyl-1-methylpiperidin-4-ol → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-7-((4-hydroxy-1-methylpiperidin-4-yl)ethynyl)-3-methylnaphthalen-2-yl)acetic acid

HRID 514081Notes

Reaction equation

HRID 514081 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:30])[C:8]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22]CC)=[O:21])=[C:9]2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[C:31]([C:33]1([OH:40])[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]1)#[CH:32]>>[C:26]([O:25][CH:19]([C:8]1[C:7]([CH3:30])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([C:32]#[C:31][C:33]3([OH:40])[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[CH:3][CH:4]=2)[C:9]=1[C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:20]([OH:22])=[O:21])([CH3:27])([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 14190994-Ethynyl-1-methylpiperidin-4-olHCID 67126201Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 671262772-Tert-butoxy-2-(1-(4-chlorophenyl)-7-((4-hydroxy-1-methylpiperidin-4-yl)ethynyl)-3-methylnaphthalen-2-yl)acetic acid

Procedure

2-tert-Butoxy-2-(1-(4-chlorophenyl)-7-((4-hydroxy-1-methylpiperidin-4-yl)ethynyl)-3-methylnaphthalen-2-yl)acetic acid (79) was prepared by the method of Example 68 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate using 4-ethynyl-1-methylpiperidin-4-ol. 1H-NMR: 400 MHz, (CD3OD) δ: 7.77 (d, J=9 Hz, 1H), 7.70 (br s, 1H), 7.58 (m, 3H), 7.41 (d, J=8 Hz, 1H), 7.30 (m, 2H), 5.16 (s, 1H), 3.35 (m, 4H), 2.89 (s, 3H), 2.60 (s, 3H), 2.15 (m, 4H), 0.98 (s, 9H). LCMS-ESI+ (m/z): [M+H]+ calcd for C31H35ClNO4: 520.2; found: 520.1.

Sources & evidence

ORD record
ord-452fcbda429e4484927c3e90295177f0
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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