Hydrochloric Acid → (4-(6-(3-Aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone hydrochloride

HRID 2271908Notes

Reaction equation

HRID 2271908 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[CH:29]=[C:28]([F:30])[C:27]([OH:31])=[C:26]([Cl:32])[CH:25]=5)[CH:22]=4)[N:17]=[CH:16][C:15]=3[C:33]([CH:35]3[CH2:37][CH2:36]3)=[O:34])=[CH:9][CH:8]=2)[CH2:3]1.Cl>CO.C(OCC)C>[ClH:32].[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[CH:29]=[C:28]([F:30])[C:27]([OH:31])=[C:26]([Cl:32])[CH:25]=5)[CH:22]=4)[N:17]=[CH:16][C:15]=3[C:33]([CH:35]3[CH2:36][CH2:37]3)=[O:34])=[CH:9][CH:8]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66716234(4-(6-(3-Aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66716423(4-(6-(3-Aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone hydrochlorideYield 276.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(4-(6-(3-aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone (15 mg, 0.03 mmol) was suspended in methanol (1 mL) at 0° C. followed by dropwise addition of HCl in diethyl ether (2 M) until complete dissolution of the solid was observed. The solvent was removed under reduced pressure to afford the desired product (23 mg, quant.) as a yellow-brown solid. 1H NMR (500 MHz, MeOD) δ 9.39 (s, 1H), 8.28-8.19 (m, 2H), 8.16 (br s, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.79 (dd, J=9.1, 2.7 Hz, 1H), 7.26-7.16 (m, 2H), 6.94 (d, J=9.2 Hz, 1H), 4.16-4.08 (m, 1H), 4.05-3.97 (m, 1H), 3.88-3.79 (m, 1H), 3.78-3.69 (m, 2H), 2.85 (br s, 1H), 2.64-2.53 (m, 1H), 2.34-2.21 (m, 1H), 1.25-1.15 (m, 4H). ESI MS m/z 518 [C28H25ClFN5O2+H]+; HPLC 98.1% (AUC), tR=5.13 min.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-05552504360c41208696e4b2d4521138
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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