4-Methylmorpholine → HCID 67089851, compound

HRID 2378743Notes

Reaction equation

HRID 2378743 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:25]=[CH:24][C:15]([C:16]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:17])=[CH:14][CH:13]=2)=[N:2]1.[CH3:26]N1CCOCC1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C[CH:57](C)[CH2:58][C:59]([NH:61][CH2:62][C:63]([OH:65])=O)=[O:60]>>[C:59]([NH:61][CH2:62][C:63]([N:21]1[CH2:22][CH2:23][N:18]([C:16](=[O:17])[C:15]2[CH:14]=[CH:13][C:12](/[CH:11]=[CH:10]/[C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][N:2]=3)=[CH:25][CH:24]=2)[CH2:19][CH2:20]1)=[O:65])(=[O:60])[CH:58]([CH3:57])[CH3:26]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 546304N-IsovaleroylglycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11427553(4-((1E)-2-(1H-Indazol-3-yl)ethenyl)phenyl)-1-piperazinylmethanone

Product 1

HCID 67089851HCID 67089851, compoundYield 38%

Procedure

The crude product (174 mg) obtained using Compound 18 (200 mg, 0.602 mmol), N-methylmorpholine (0.132 mL, 1.20 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (161 mg, 0.842 mmol), 1-hydroxybenzotriazole monohydrate (106 mg, 0.783 mmol) and (3-methylbutyrylamino)acetic acid (115 mg, 0.722 mmol) in a similar manner to Example 5, was purified by silica gel column chromatography (chloroform/methanol=80/20), followed by triturating in mixed solvent of ethyl acetate/ethanol to obtain Compound 126 (105 mg, 37%).

Workup

  1. customwas purified by silica gel column chromatography (chloroform/methanol=80/20)
  2. customby triturating in mixed solvent of ethyl acetate/ethanol

Sources & evidence

ORD record
ord-b28712e3b6984b99bf152698ac18ca1e
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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