Cyclopropylacetylene → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(2-cyclopropylethyl)-7-methylquinolin-6-yl)acetic acid

HRID 931799Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH2:21][CH2:22][C:23]1[CH:28]=CC=C[CH:24]=1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(C1CC1)#C>>[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH2:21][CH2:22][CH:23]1[CH2:28][CH2:24]1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 2

HCID 138823Cyclopropylacetylene

HCID 56645258(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)acetic acid

Product 1

HCID 56593456(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(2-cyclopropylethyl)-7-methylquinolin-6-yl)acetic acid

Procedure

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-2-(2-cyclopropylethyl)-7-methylquinolin-6-yl)acetic acid (39) (5.7 mg) was prepared in a similar manner as compound (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)acetic acid of Example 37 except using ethynylcyclopropane instead of ethynylbenzene. 1H-NMR 400 MHz (CD3OD) δ 8.17 (d, J=8.4 Hz, 1 H), 7.91 (s, 1 H), 7.66 (d, J=8.8 Hz, 1 H), 7.6-7.5 (m, 3 H), 7.31 (m, 1 H), 5.18 (s, 1 H), 3.21 (m, 2 H), 2.71 (s, 3 H), 1.72 (m, 2 H), 0.92 (s, 9 H), 0.75 (m, 1 H), 0.41 (m, 2 H), 0.02 (m, 2 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C27H31ClNO3: 452.2. Found: 452.2.

Sources & evidence

ORD record: ord-20450a2ab72f4ea0b87a6561f0d39cf5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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