4-Methylmorpholine → HCID 67089612, compound

HRID 2378739Notes

Reaction equation

HRID 2378739 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.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[N:51]1([CH2:57][C:58]([N:60]2[CH2:64][CH2:63][CH2:62][CH2:61]2)=[O:59])[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1>>[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:54]3[CH2:53][CH2:52][N:51]([CH2:57][C:58](=[O:59])[N:60]4[CH2:61][CH2:62][CH2:63][CH2:64]4)[CH2:56][CH2:55]3)=[O:18])=[CH:19][CH:20]=2)=[N:2]1

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 1006141-((Pyrrolidine-1-carbonyl)methyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11437002(E)-4-(2-(1H-indazol-3-yl)vinyl)benzoic acid

Product 1

HCID 67089612HCID 67089612, compoundYield 60%

Procedure

The crude product obtained using (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid (300 mg, 1.14 mmol) obtained in Step 6 of Example 1, N-methylmorpholine (0.25 mL, 2.28 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (305 mg, 1.59 mmol), 1-hydroxybenzotriazole monohydrate (200 mg, 1.48 mmol) and 2-(piperazin-1-yl)-1-(pyrrolidin-1-yl)ethanone (337 mg, 1.71 mmol) in a similar manner to Step 7 of example 1, was triturated in mixed solvent of ethyl acetate/methanol to obtain Compound 121 (298 mg, 60%).

Workup

  1. customwas triturated in mixed solvent of ethyl acetate/methanol

Sources & evidence

ORD record
ord-43bf09a71b844ff3903d17e1f3ce8d46
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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