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

HRID 931798Notes

Reaction equation

HRID 931798 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]([C:21]#[C:22][C:23]1[CH:28]=[CH:27]C=CC=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: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]([C:21]#[C:22][CH:23]1[CH2:27][CH2:28]1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 138823CyclopropylacetyleneHCID 56645057(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)acetic acid

Product 1

HCID 56645257(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(cyclopropylethynyl)-7-methylquinolin-6-yl)acetic acid

Procedure

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-2-(cyclopropylethynyl)-7-methylquinolin-6-yl)acetic acid (38) (5.5 mg) was prepared in a similar manner as compound (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)acetic acid of Example 37 except using ethynylcyclopropane instead of ethynylbenzene. 1H-NMR 400 MHz (CD3OD) 8.0 (m, 1 H), 7.84 (s, 1 H), 7.64-7.55 (4 H, m), 7.35 (d, J=7.6 Hz, 1H), 5.21 (s, 1 H), 2.72 (s, 3 H), 1.65 (m, 1 H), 1.13-1.02 (m, 4 H), 0.98 (s, 9 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C27H27ClNO3: 448.2. Found: 448.2.

Sources & evidence

ORD record
ord-124535f66316446e9e82ebd6e7adc532
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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