Hydrochloric Acid → (R)-8-Hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

HRID 1853755Notes

Reaction equation

HRID 1853755 reaction equation
Br.[OH:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[NH:9][C:8](=[O:14])[C:7]3[S:15][CH:16]=[CH:17][C:6]=3[C:5]=2[C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([CH3:28])[CH2:25][NH:26][CH3:27])=[CH:20][CH:19]=1.[ClH:29]>>[ClH:29].[OH:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[NH:9][C:8](=[O:14])[C:7]3[S:15][CH:16]=[CH:17][C:6]=3[C:5]=2[C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([CH3:28])[CH2:25][NH:26][CH3:27])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67450338HCID 67450338, compound

Product 1

HCID 67449409(R)-8-Hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Procedure

Following General Procedure D-3, (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one hydrobromide (120 mg, 0.26 mmol) was dissolved in aqueous HCl (100 mmol) and stirred concentrated at room temperature for 2 h, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt. The desired product was dried under high vacuum to afford the desired product as a light yellow solid (27 mg, 28%): 1H NMR (500 M Hz, CD3OD) δ 7.61-7.53 (m, 2H), 7.46 (dd, J=7.8, 1.8 Hz, 1H), 7.36 (dd, J=7.9, 1.6 Hz, 1H), 7.31 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (s, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.41-3.24 (m, 3H), 2.74 (s, 3H), 2.57 (s, 3H), 1.50 (d, J=6.8 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC 98.7% (AUC), tR=8.82 min.

Workup

  1. concentrationconcentrated at room temperature for 2 h
  2. concentrationconcentrated
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-ea2daeb8fed64d4190f91953ec404acb
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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