Hydrochloric Acid → HCID 69588731, compound

HRID 1241450Notes

Reaction equation

HRID 1241450 reaction equation
[ClH:1].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C@@H:11]([CH2:18][C:19]3[N:20]=[C:21]([CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]4[CH:34]=[C:33]([N:35]5[CH2:40][CH2:39][O:38][CH2:37][CH2:36]5)[CH:32]=[CH:31][N:30]=4)[S:22][CH:23]=3)[CH2:12][C:13]([O:15]CC)=[O:14])=[CH:10][C:5]=2[O:4][CH2:3]1.[Li+].[OH-].Cl>C1COCC1>[ClH:1].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C@@H:11]([CH2:18][C:19]3[N:20]=[C:21]([CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]4[CH:34]=[C:33]([N:35]5[CH2:36][CH2:37][O:38][CH2:39][CH2:40]5)[CH:32]=[CH:31][N:30]=4)[S:22][CH:23]=3)[CH2:12][C:13]([OH:15])=[O:14])=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86595789HCID 86595789, compound

Product 1

HCID 69588731HCID 69588731, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3S)-Ethyl 3-(1,3-benzodioxol-5-yl)-4-(2-{4-[(4-morpholin-4-ylpyridin-2-yl)amino]butyl}-1,3-thiazol-4-yl)butanoate hydrochloride (0.50 mmol) was dissolved in THF (2 mL) at 0° C. 1M LiOH (2.5 mL) was added, and the reaction was warmed to room temperature and stirred for 20 hours. The reaction was acidified to pH=1 with conc. HCl and concentrated in vacuo. The residue was purified via reverse phase HPLC using a gradient of 5–50% CH3CN/H2O/0.5% HCl over 30 minutes to obtain the desired product. Yield: 83 mg, 28% over 2 steps. 1H NMR (DMSO-d6) δ7.63–7.68 (m, 1H), 7.01–7.04 (m, 1H), 6.85–6.82 (m, 1H), 6.75–6.71 (m, 1H), 6.65–6.59 (m, 1H), 6.59–6.54 (m, 1H), 6.03–5.98 (m, 1H), 5.97 (s, 2H), 3.73–3.66 (m, 4H), 3.52–3.45 (m, 4H), 3.50–3.38 (m, 5H), 3.33–3.25 (m, 2H), 3.06–2.87 (m, 4H), 2.62–2.46 (m, 2H), 1.84–1.73 (m, 2H), 1.65–1.55 (m, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified via reverse phase HPLC
  3. customover 30 minutes

Sources & evidence

ORD record
ord-c0f32f1f602f4752a87dca7e0e1b3c47
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

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