Hydrochloric Acid → HCID 25095507, compound
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)=[N:2]1.[NH:21]1[CH2:25][CH2:24][C@@H:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1.Cl>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([C:16]([N:21]3[CH2:25][CH2:24][C@@H:23]([NH2:26])[CH2:22]3)=[O:18])=[CH:19][CH:20]=2)=[N:2]1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
The product obtained using (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid (700 mg, 2.65 mmol) obtained in Step 6 of Example 1, tert-butyl (R)-(pyrrolidin-3-yl)carbamate (740 mg, 3.98 mmol), 1-hydroxybenzotriazole monohydrate (470 mg, 3.46 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (710 mg, 3.72 mmol) and N-methylmorpholine (0.608 mL, 5.32 mmol) in a similar manner to Example 5, was dissolved in methanol (1.5 mL), and the solution was added with a 4 mol/L solution of hydrogen chloride in methanol (1.50 mL), followed by heating under reflux at 60° C. for 60 minutes. The reaction mixture was concentrated under reduced pressure, the residue was added with saturated aqueous potassium carbonate solution and ethyl acetate and was extracted. The crude product was crystallized from ethyl acetate to obtain Compound 158 (506 mg, 58%).
Workup
- customThe product obtained
- temperatureby heating
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionthe residue was added with saturated aqueous potassium carbonate solution and ethyl acetate
- extractionwas extracted
- customThe crude product was crystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-e6a6ea02b4184acfb3229c584a39f41a
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470717B2
Reaction notes
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