Hydrochloric Acid → HCID 69588557, compound

HRID 1241436Notes

Reaction equation

HRID 1241436 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([CH:14]([CH2:21][C:22]3[N:23]=[C:24]([CH2:27][CH2:28][CH2:29][C:30]4[CH:39]=[CH:38][C:37]5[CH2:36][CH2:35][CH2:34][NH:33][C:32]=5[N:31]=4)[S:25][CH:26]=3)[CH2:15][C:16]([O:18]CC)=[O:17])=[CH:12][N:13]=2)=[CH:5][CH:4]=1.[Li+].[OH-].Cl>C1COCC1>[ClH:2].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([CH:14]([CH2:21][C:22]3[N:23]=[C:24]([CH2:27][CH2:28][CH2:29][C:30]4[CH:39]=[CH:38][C:37]5[CH2:36][CH2:35][CH2:34][NH:33][C:32]=5[N:31]=4)[S:25][CH:26]=3)[CH2:15][C:16]([OH:18])=[O:17])=[CH:12][N:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21934519HCID 21934519, compound

Product 1

HCID 69588557HCID 69588557, compoundYield 295.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-[2-(4-chlorophenyl)-1,3-thiazol-5-yl]-4-{2-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl )propyl]-1,3-thiazol-4-yl}butanoate hydrochloride (Scheme 3, Step 2), (180 mg, 0.281 mmol) was dissolved in THF. Upon cooling to 0° C., 0.84 mL LiOH (1M) was added and allowed to stir at room temperature overnight. The reaction was acidified to pH=1 with HCl and concentrated in vacuo. The residue was purified via reverse phase HPLC to yield the title compound (239 mg, 78%). 1H NMR (DMSO-d6) δ1.77–1.87 (m, 2H), 2.02–2.12 (m, 2H), 2.61–2.82 (m, 6H), 2.95–3.18 (m, 4H), 3.39–3.45 (m, 2H), 3.85–3.95 (m, 1H), 6.55 (d, 1H), 7.18 (s, 1H), 7.48–7.54 (m, 2H), 7.56 (d, 1H), 7.62 (s, 1H), 7.80–7.85 (m, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-e4e8b229c3d341adaf638716491e858f
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

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