Hydrochloric Acid → HCID 178478724, compound

HRID 2271718Notes

Reaction equation

HRID 2271718 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[CH:24]=[C:23]([Cl:25])[C:22]([OH:26])=[C:21]([Cl:27])[CH:20]=4)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:28]([CH:30]2[CH2:32][CH2:31]2)=[O:29])[CH2:4][CH2:3]1.[ClH:33]>CO>[ClH:25].[ClH:33].[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([Cl:27])[C:22]([OH:26])=[C:23]([Cl:25])[CH:24]=4)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:28]([CH:30]2[CH2:31][CH2:32]2)=[O:29])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178511646HCID 178511646, compound

Product 1

HCID 178478724HCID 178478724, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of {4-[trans-4-aminocyclohexylamino]-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-3-yl}(cyclopropyl)methanone (9.1 mg, 0.019 mmol) in methanol (10 mL) was treated with 1 N HCl (2 mL) and the mixture was concentrated and dried to obtain the desired salt (7.7 mg, 77%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.38 (s, 1H), 8.46 (s, 1H), 8.28 (d, J=8.5 Hz, 1H), 7.99 (d, J=8.5 Hz, 1H), 7.75 (bs, 2H), 2.86 (bs, 1H), 2.54-2.48 (m, 2H), 2.25-2.19 (m, 2H), 1.87-1.79 (m, 2H), 1.72-1.50 (m, 2H), 1.40-1.18 (m, 4H); ESI MS m/z 470 [C25H25Cl2N3O2+H]+; HPLC 95.0% (AUC), tR=10.79 min.

Workup

  1. concentrationthe mixture was concentrated
  2. customdried

Sources & evidence

ORD record
ord-e3873249963243d4992e965949f96d40
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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