4-Methylmorpholine → HCID 67089715, compound

HRID 2378751Notes

Reaction equation

HRID 2378751 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](/[CH:24]=[CH:25]/[C:26]2[CH:39]=[CH:38][C:29]([C:30]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[O:31])=[CH:28][CH:27]=2)=[N:16]1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[C:70]([N:73]([CH2:75][C:76](O)=[O:77])[CH3:74])(=[O:72])[CH3:71]>>[C:70]([N:73]([CH2:75][C:76]([N:35]1[CH2:36][CH2:37][N:32]([C:30](=[O:31])[C:29]2[CH:28]=[CH:27][C:26](/[CH:25]=[CH:24]/[C:17]3[C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[NH:15][N:16]=3)=[CH:39][CH:38]=2)[CH2:33][CH2:34]1)=[O:77])[CH3:74])(=[O:72])[CH3:71]

Participants

7

Reactant 6

HCID 79724-MethylmorpholineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10975514N-Acetyl-N-methylglycineHCID 11427553(4-((1E)-2-(1H-Indazol-3-yl)ethenyl)phenyl)-1-piperazinylmethanone

Product 1

HCID 67089715HCID 67089715, compoundYield 25%

Procedure

The crude product obtained using dihydrochloride of Compound 18 (300 mg, 0.741 mmol), N-methylmorpholine (0.163 mL, 1.48 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (199 mg, 1.04 mmol), 1-hydroxybenzotriazole monohydrate (130 mg, 0.963 mmol) and N-acetylsarcosine (77.7 mg, 0.593 mmol) In a similar manner to Example 5, was purified by silica gel column chromatography (chloroform/methanol=90/10), followed by triturating in mixed solvent of ethyl acetate/methanol to obtain Compound 138 (54.8 mg, 25%).

Workup

  1. customwas purified by silica gel column chromatography (chloroform/methanol=90/10)
  2. customby triturating in mixed solvent of ethyl acetate/methanol

Sources & evidence

ORD record
ord-8171c0ec3d2d49edbb373fc8a56fffa3
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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