4-Methylmorpholine → HCID 68779800, compound

HRID 1971769Notes

Reaction equation

HRID 1971769 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]([CH3:20])[C:8]([NH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)=[O:9].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:45][C:46]1[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][C:47]=1[NH:53][C:54](=[O:60])[O:55][C:56]([CH3:59])([CH3:58])[CH3:57].CN1CCOCC1>CN(C=O)C.O.C(#N)C>[F:52][C:50]1[CH:49]=[CH:48][C:47]([NH:53][C:54](=[O:60])[O:55][C:56]([CH3:57])([CH3:59])[CH3:58])=[C:46]([NH:45][C:15](=[O:17])[C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:8](=[O:9])[CH:7]([N:3]3[CH2:4][CH2:5][CH2:6][C:2]3=[O:1])[CH3:20])=[CH:19][CH:18]=2)[CH:51]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24688763N1-(tert-Butoxycarbonyl)-4-fluoro-1,2-phenylenediamineHCID 68776068HCID 68776068, compound

Product 1

HCID 68779800HCID 68779800, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

To the 4-(2-(2-oxopyrrolidin-1-yl)propanamido)benzoic acid (210 mgs, 0.76 mmol) in DMF (2 mL), was added HATU (375 mg, 0.99 mmol), tert-butyl 2-amino-4-fluorophenylcarbamate (172 mg, 0.76 mmol) and NMM (0.3 mL, 2.3 mmol) and stirred at 55° C. for 40 hours. The reaction mixture was then diluted with water and acetonitrile and the precipitate formed was then filtered, washed with water and dried. The solid was then purified by column chromatography on silica gel with elution using 80% ethyl acetate/hexanes to give tert-butyl 4-fluoro-2-(4-(2-(2-oxopyrrolidin-1-yl)propanamido)benzamido)phenylcarbamate.

Workup

  1. customthe precipitate formed
  2. filtrationwas then filtered
  3. washwashed with water
  4. customdried
  5. customThe solid was then purified by column chromatography on silica gel with elution

Sources & evidence

ORD record
ord-dfb67a63a4d240599b33a78923741697
Source dataset
uspto-grants-2013_04
Patent number
US08431610B2

Reaction notes

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