4-Methylmorpholine → HCID 67090328, 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.CN1CCOCC1.[ClH:28].C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH:51]([NH:54][C:55](=[O:63])[CH2:56][N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1)([CH3:53])[CH3:52].C(OCC)(=O)C.Cl>C(Cl)(Cl)Cl.CO>[ClH:28].[ClH:28].[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:60]3[CH2:59][CH2:58][N:57]([CH2:56][C:55](=[O:63])[NH:54][CH:51]([CH3:52])[CH3:53])[CH2:62][CH2:61]3)=[O:18])=[CH:19][CH:20]=2)=[N:2]1Participants
8
Reactant 6
HCID 79724-Methylmorpholine
HCID 100826N-isopropyl-1-piperazineacetamide
HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
HCID 27960291-Hydroxybenzotriazole hydrate
HCID 11437002(E)-4-(2-(1H-indazol-3-yl)vinyl)benzoic acid
HCID 21866389Hydrogen chloride-ethyl acetateProduct 1
Reagents, catalysts & solvents 1
Procedure
The crude product obtained using (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid (200 mg, 0.757 mmol) obtained in Step 6 of Example 1, N-methylmorpholine (0.166 mL, 1.51 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (203 mg, 1.06 mmol), 1-hydroxybenzotriazole monohydrate (133 mg, 0.984 mmol) and-N-isopropyl-2-(piperazin-1-yl)acetamide (210 mg, 1.14 mmol) in a similar manner to Step 7 of Example 1, was purified by silica gel column chromatography (chloroform/methanol=80/20), followed by treating with 4 mol/L hydrogen chloride-ethyl acetate solution (0.665 mL) to obtain Compound 135 (99.7 mg, 26%).
Sources & evidence
- ORD record
- ord-bccc0877d9654120ab336e6d83216bcb
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470717B2
Reaction notes
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