Hydrochloric Acid → HCID 86692958, compound

HRID 2271815Notes

Reaction equation

HRID 2271815 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([C:20](=[O:24])[CH2:21][CH2:22][CH3:23])=[C:13]3[NH:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][N:33]([CH3:35])[CH3:34])=[CH:28][CH:27]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].[ClH:36].CCOCC>CO>[ClH:1].[ClH:36].[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([C:20](=[O:24])[CH2:21][CH2:22][CH3:23])=[C:13]3[NH:25][C:26]2[CH:27]=[CH:28][C:29]([CH2:32][N:33]([CH3:35])[CH3:34])=[CH:30][CH:31]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68091941HCID 68091941, compound

Product 1

HCID 86692958HCID 86692958, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-(6-(3,5-dichloro-4-hydroxyphenyl)-4-((4-((dimethylamino)methyl)phenyl)amino)quinolin-3-yl) butan-1-one (6.5 mg, 0.0082 mmol) in methanol (4 mL) was added 2N HCl in ether (2.0 mL, 4 mmol). The resultant clear yellow solution was concentrated to afford the desired product as a yellow solid. 1H NMR (500 MHz, MeOD) δ 9.35 (s, 1H), 8.23 (dd, J=8.8, 1.9 Hz, 1H), 8.03 (d, J=8.8 Hz, 1H), 7.85 (d, J=1.9 Hz, 1H), 7.78-7.72 (m, 2H), 7.65-7.58 (m, 2H), 7.18 (s, 2H), 4.48 (s, 2H), 3.20 (t, J=7.2 Hz, 2H), 2.88 (s, 6H), 1.81 (h, J=7.3 Hz, 2H), 1.07 (t, J=7.4 Hz, 3H). ESI MS m/z 508 [C28H27Cl2N3O2+H]+; HPLC 93.5% (AUC), tR=11.88 min.

Workup

  1. concentrationThe resultant clear yellow solution was concentrated

Sources & evidence

ORD record
ord-4798344045ca4aaba1058c0298daba7f
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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