3-Butyn-2-amine, 2-methyl- → HCID 56600131, compound

HRID 514087Notes

Reaction equation

HRID 514087 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.[CH3:31][C:32]([NH2:36])([C:34]#[CH:35])[CH3:33]>>[NH2:36][C:32]([CH3:33])([CH3:31])[C:34]#[C:35][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:30])[C:8]([CH:19]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])[C:20]([OH:22])=[O:21])=[C:9]2[C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 763193-Butyn-2-amine, 2-methyl-HCID 67126201Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 56600131HCID 56600131, compound

Procedure

2-(7-(3-Amino-3-methylbut-1-ynyl)-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid (85) was prepared by the method of Example 67 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate using 2-methylbut-3-yn-2-amine. 1H-NMR: 400 MHz, (CD3OD) δ: 7.81 (d, J=8 Hz, 1H), 7.72 (s, 1H), 7.57 (m, 3H), 7.45 (d, J=8 Hz, 1H), 7.35 (s, 1H), 7.30 (d, J=8 Hz, 1H), 5.16 (s, 1H), 2.62 (s, 3H), 1.68 (s, 6H), 0.98 (s, 9H). LCMS-ESI+ (m/z): [M—NH2]+ calcd for C28H28ClO3: 447.2; found: 446.9.

Sources & evidence

ORD record
ord-c9ab49be60944e4782ee2e25f37375ac
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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