Trifluoroacetic acid → [6-(3-Chloro-4-hydroxy-5-methoxyphenyl)-4-(2,8-diazaspiro[4,5]decan-8-yl)quinolin-3-yl](cyclopropyl)methanone

HRID 2271732Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21]([CH:23]2[CH2:25][CH2:24]2)=[O:22])=[C:14]3[N:26]2[CH2:42][CH2:41][C:29]3([CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]3)[CH2:28][CH2:27]2)[CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8].C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21]([CH:23]2[CH2:24][CH2:25]2)=[O:22])=[C:14]3[N:26]2[CH2:42][CH2:41][C:29]3([CH2:33][NH:32][CH2:31][CH2:30]3)[CH2:28][CH2:27]2)[CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68091922tert-Butyl 8-[6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-yl]-2,8-diazaspiro[4,5]decane-2-carboxylate

Product 1

HCID 66715553[6-(3-Chloro-4-hydroxy-5-methoxyphenyl)-4-(2,8-diazaspiro[4,5]decan-8-yl)quinolin-3-yl](cyclopropyl)methanoneYield 38%

Procedure

Following general procedure A-2, tert-butyl 8-[6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-yl]-2,8-diazaspiro[4,5]decane-2-carboxylate (110 mg, 0.097 mmol) was reacted with TFA (2 mL) to afford the desired product (18 mg, 38%) as a green solid: 1H NMR (300 MHz, CD3OD) δ 8.79 (s, 1H), 8.29 (s, 1H), 8.02 (s, 2H), 7.30 (d, J=2.1 Hz, 1H), 7.23 (d, J=2.1 Hz, 1H), 3.98 (s, 4H), 3.08 (s, 2H), 2.65-2.52 (m, 1H), 2.03-1.81 (m, 7H), 1.37-1.16 (m, 8H); ESI MS m/z 492 [C28H30ClN3O3+H]+.

Sources & evidence

ORD record: ord-83c6ad2ef62a4a588f5728686a7cfbba
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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