3-Butyn-2-amine, 2-methyl- → 2-(7-(3-Amino-3-methylbut-1-ynyl)-1-(chroman-6-yl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid

HRID 514088Notes

Reaction equation

HRID 514088 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:27])[C:8]([C:20](=[O:26])[C:21]([O:23]CC)=[O:22])=[C:9]2OS(C(F)(F)F)(=O)=O)=[CH:4][CH:3]=1.[O:28]1[C:37]2[C:32](=[CH:33][C:34](B(O)O)=[CH:35][CH:36]=2)[CH2:31][CH2:30][CH2:29]1.[CH3:41][C:42]([NH2:46])([C:44]#[CH:45])[CH3:43]>>[NH2:46][C:42]([CH3:43])([CH3:41])[C:44]#[C:45][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:27])[C:8]([CH:20]([O:26][C:5]([CH3:10])([CH3:6])[CH3:4])[C:21]([OH:23])=[O:22])=[C:9]2[C:34]2[CH:33]=[C:32]3[C:37](=[CH:36][CH:35]=2)[O:28][CH2:29][CH2:30][CH2:31]3)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 763193-Butyn-2-amine, 2-methyl-HCID 50990450(3,4-dihydro-2H-1-benzopyran-6-yl)boronic acidHCID 86691550Ethyl 2-(7-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

Product 1

HCID 671262382-(7-(3-Amino-3-methylbut-1-ynyl)-1-(chroman-6-yl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid

Procedure

2-(7-(3-Amino-3-methylbut-1-ynyl)-1-(chroman-6-yl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid (87) was prepared by the method of Example 67 from ethyl 2-(7-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate using chroman-6-ylboronic acid. The remainder of the sequence follows the method of Example 67 using 2-methylbut-3-yn-2-amine in Step 7. 1H-NMR: 400 MHz, (CD3OD) δ: 7.77 (d, J=8 Hz, 1H), 7.66 (s, 1H), 7.48 (s, 1H), 7.45 (m, 1H), 7.23 (m, 1H), 6.90 (m, 2H), 5.31 (s, 1H), 4.28 (t, J=5 Hz, 1H), 2.87 (m, 2H), 2.58 (s, 3H), 2.08 (m, 2H), 1.68 (s, 6H), 0.99 (s, 9H). LCMS-ESI+ (m/z): [M—NH2]+ calcd for C31H33O4: 469.2; found: 469.2.

Sources & evidence

ORD record
ord-9e3a45ece3c646f7a642720b10369b4b
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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