4-Methylmorpholine → (E)-N-(2-aminoethyl)-4-[2-(1H-indazol-3-yl)vinyl]benzamide dihydrochloride

HRID 2378737Notes

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.C(OC(=O)[NH:27][CH2:28][CH2:29][NH2:30])(C)(C)C.O.ON1C2C=CC=CC=2N=N1.[ClH:43].C(N=C=NCCCN(C)C)C.CN1CCOCC1.Cl.CO>CO>[ClH:43].[ClH:43].[NH2:27][CH2:28][CH2:29][NH:30][C:16](=[O:18])[C:15]1[CH:14]=[CH:13][C:12](/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The product obtained using (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid (300 mg, 1.00 mmol) obtained in Step 6 of Example 1, N-(2-aminoethyl)carbamic acid tert-butyl ester (240 mg, 1.50 mmol), 1-hydroxybenzotriazole monohydrate (176 mg, 1.30 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (270 mg, 1.40 mmol) and N-methylmorpholine (0.22 mL, 2.00 mmol) in a similar manner to Example 5, was dissolved in methanol (2.00 mL), and the solution was added with 4 moL/L hydrogen chloride-methanol solution (1.50 mL), followed by heating under reflux at 60° C. for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from acetone to obtain Compound 111 (206 mg, 54%).

Workup

customThe product obtained
temperatureby heating
concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was crystallized from acetone

Sources & evidence

ORD record: ord-3e93c5e649514cc8bde499469c9256e1
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470717B2

Reaction notes

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