Hydrochloric Acid → HCID 66715845, compound

HRID 2271960Notes

Reaction equation

HRID 2271960 reaction equation
[NH2:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]4[CH:27]=[C:26]([Cl:28])[C:25]([OH:29])=[C:24]([Cl:30])[CH:23]=4)[CH:20]=3)[N:15]=[CH:14][C:13]=2[C:31]([CH:33]2[CH2:35][CH2:34]2)=[O:32])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].Cl>CO.CCOCC>[ClH:28].[NH2:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]4[CH:23]=[C:24]([Cl:30])[C:25]([OH:29])=[C:26]([Cl:28])[CH:27]=4)[CH:20]=3)[N:15]=[CH:14][C:13]=2[C:31]([CH:33]2[CH2:34][CH2:35]2)=[O:32])=[CH:9][CH:10]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66715213HCID 66715213, compound

Product 1

HCID 66715845HCID 66715845, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherCatalystHCID 887MethanolSolvent

Procedure

To a suspension of {4-[4-(2-aminopropan-2-yl)phenylamino]-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-3-yl}(cyclopropyl)methanone (14 mg, 0.028 mmol) in methanol (5 mL) was added HCl in ether (3 drops, 2 M). The resultant solution was concentrated to obtain the desired product as the hydrochloride salt (13 mg) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.31 (s, 1H), 8.24-8.22 (m, 1H), 8.18 (s, 1H), 8.04 (d, J=8.8 Hz, 1H), 7.65 (d, J=9.0 Hz, 2H), 7.49 (d, J=9.0 Hz, 2H), 7.42 (s, 2H), 2.84-2.75 (m, 1H), 1.78 (s, 6H), 1.18-1.09 (m, 4H); ESI MS m/z 506 [C28H25Cl2N3O2+H]+; HPLC 98.5% (AUC), tR=10.80 min.

Workup

  1. concentrationThe resultant solution was concentrated

Sources & evidence

ORD record
ord-5891b47cc37c43feb1ee922d613c2622
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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