4-Methylmorpholine → HCID 67090247, compound

HRID 2378754Notes

Reaction equation

HRID 2378754 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:13].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.[OH:70][CH2:71][CH2:72][N:73]([CH2:77][C:78](O)=[O:79])[CH2:74][CH2:75][OH:76]>>[ClH:13].[ClH:13].[OH:76][CH2:75][CH2:74][N:73]([CH2:72][C:71]([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:70])[CH2:77][CH2:78][OH:79]

Participants

7

Reactant 6

HCID 79724-MethylmorpholineHCID 8761BicineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 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 67090247HCID 67090247, compoundYield 21%

Procedure

The crude product obtained using dihydrochloride of Compound 18 (150 mg, 0.370 mmol) N-methylmorpholine (0.0812 mL, 0.740 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (99.3 mg, 0.370 mmol), 1-hydroxybenzotriazole monohydrate (64.9 mg, 0.481 mmol) and di(hydroxyethyl)aminoacetic acid (60.4 mg, 0.370 mmol) in a similar manner to Example 5, was purified by C-18 column chromatography (water/methanol=67/33), followed by treating with 10% hydrogen chloride-methanol solution (0.775 mL) and triturating in ethyl acetate to obtain Compound 144 (43.5 mg, 21%).

Workup

  1. customwas purified by C-18 column chromatography (water/methanol=67/33)
  2. additionby treating with 10% hydrogen chloride-methanol solution (0.775 mL)
  3. customtriturating in ethyl acetate

Sources & evidence

ORD record
ord-8f78b6059a574320ba3ab21cec4c5368
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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