1-Ethynylcyclohexylamine → HCID 56599939, compound

HRID 514086Notes

Reaction equation

HRID 514086 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([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)#[CH:32]>>[NH2:39][C:33]1([C:31]#[C:32][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([CH3:30])[C:8]([CH:19]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])[C:20]([OH:22])=[O:21])=[C:9]3[C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)=[CH:4][CH:3]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 1216911-EthynylcyclohexylamineHCID 67126201Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 56599939HCID 56599939, compound

Procedure

2-(7-((1-Aminocyclohexyl)ethynyl)-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid (84) was prepared by the method of Example 67 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate using 1-ethynylcyclohexanamine. 1H-NMR: 400 MHz, (CD3OD) δ: 7.82 (d, J=8 Hz, 1H), 7.72 (s, 1H), 7.56 (m, 3H), 7.47 (d, J=8 Hz, 1H), 7.37 (s, 1H), 7.31 (d, J=8 Hz, 1H), 5.20 (s, 1H), 2.60 (s, 3H), 2.11 (m, 2H), 1.63-1.85 (m, 8H), 0.99 (s, 9H). LCMS-ESI+ (m/z): [M—NH2]+ calcd for C31H32ClO3: 487.2; found: 487.2.

Sources & evidence

ORD record
ord-a41bd1725697462795bbdef31dc80ea4
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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