Hydrochloric Acid → HCID 86700045, compound

HRID 1428096Notes

Reaction equation

HRID 1428096 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:31]=[CH:30][C:14]([CH2:15][N:16]2[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[C:19](=[O:26])[C:18]([C:27](O)=[O:28])=[CH:17]2)=[CH:13][CH:12]=1.CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.[CH3:59][C@H:60]1[O:65][C@@H:64]([CH3:66])[CH2:63][NH:62][CH2:61]1.Cl>CN(C=O)C>[CH3:66][C@H:64]1[O:65][C@@H:60]([CH3:59])[CH2:61][N:62]([C:27]([C:18]2[C:19](=[O:26])[C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:21][N:16]([CH2:15][C:14]3[CH:30]=[CH:31][C:11]([F:10])=[CH:12][CH:13]=3)[CH:17]=2)=[O:28])[CH2:63]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 6415002,6-Dimethylmorpholine, cis-HCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 86700046HCID 86700046, compound

Product 1

HCID 86700045HCID 86700045, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (228 μl) was added to a solution of the compound obtained in Step 2 of Example 26 (200 mg) and COMU (365 mg) in DMF (2.5 ml) at room temperature, and the mixture was stirred for 15 minutes. cis-2,6-Dimethylmorpholine (162 μl) was added and the mixture was stirred for four hours. A 1 N hydrochloric acid solution was added at room temperature, and the organic layer was extracted with ethyl acetate, washed with brine and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->30:1 (v/v)] to give 30 mg of the title compound as an oily substance.

Workup

  1. stirringthe mixture was stirred for four hours
  2. extractionthe organic layer was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [chloroform:methanol=300:1->30:1 (v/v)]

Sources & evidence

ORD record
ord-60799f7a09484c30a4b32faf00f78761
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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