Morpholine → HCID 71288657, compound

HRID 1621119Notes

Reaction equation

HRID 1621119 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:23])[NH:8][CH2:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[C:5]([C:24](O)=[O:25])[CH:4]=[N:3]1.CCOC(C(C#N)=NOC([N:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.N1CCOCC1>CN(C=O)C>[CH3:16][C:15]1[O:14][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:12][C:11]=1[CH2:10][CH2:9][NH:8][C:7]([C:6]1[N:2]([CH3:1])[N:3]=[CH:4][C:5]=1[C:24]([N:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1)=[O:25])=[O:23]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531Diisopropylethylamine2×HCID 71279111HCID 71279111, compoundHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate

Product 1

HCID 71288657HCID 71288657, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-methyl-5-(2-(5-methyl-2-phenyloxazol-4-yl)ethylcarbamoyl)-1H-pyrazole-4-carboxylic acid (40 mg, 113 μmol) in DMF (1 mL) were added COMU (58.0 mg, 135 μmol) and N,N-diisopropylethylamine (14.6 mg, 19.7 μL, 113 μmol) at 0-5° C. After 10 min the suspension became a clear solution and subsequently morpholine (11.8 mg, 135 μmol) and N,N-diisopropylethylamine (14.6 mg, 19.7 μL, 113 μmol) were added. The ice bath was removed after 10 min and the mixture was stirred at RT for 3 h. The product was obtained after purification by preparative HPLC using an acetonitrile/water (containing 0.1% formic acid) gradient as off-white waxy solid (31 mg, 73.2 μmol, 64.9%).

Workup

  1. customThe ice bath was removed after 10 min
  2. customThe product was obtained
  3. customafter purification by preparative HPLC

Sources & evidence

ORD record
ord-43f11731740f42e1867eaac8d29e2860
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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