Morpholine → HCID 178481612, compound

HRID 538058Notes

Reaction equation

HRID 538058 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:5]=2[N:4]([CH2:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([C:22](O)=[O:23])[CH2:18][CH2:17]2)[C:3]1=[O:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1.C(N(CC)CC)C.[Cl-].[NH4+]>CS(C)=O.C(Cl)Cl>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([F:12])([F:14])[F:13])=[CH:10][C:5]=2[N:4]([CH2:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]([N:50]3[CH2:55][CH2:54][O:53][CH2:52][CH2:51]3)=[O:23])[CH2:18][CH2:17]2)[C:3]1=[O:25]

Participants

8

Reactant 5

HCID 8083MorpholineHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178481613HCID 178481613, compound

Product 1

HCID 178481612HCID 178481612, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

trans-4-(3-Methyl-2-oxo-6-trifluoromethyl-2,3-dihydro-benzoimidazol-1-ylmethyl)cyclohexanecarboxylic acid (78 mg, 0.22 mmol), HATU (100 mg, 0.26 mmol), morpholine (23 mg, 0.26 mmol) and triethyl amine (0.04 ml, 0.26 mmol) were dissolved in DMSO and the mixture were shaken overnight. 3 ml of a saturated solution of ammonium chloride and 2 ml of DCM were added and the organic layer was separated and washed with water. The organic solvent was evaporated and the crude was purified by silica column using ethyl acetate as eluent. 25 mg (yield 27%) of the titled compound were isolated.

Workup

  1. customthe organic layer was separated
  2. washwashed with water
  3. customThe organic solvent was evaporated
  4. customthe crude was purified by silica column

Sources & evidence

ORD record
ord-bdc7b1a0597d4ed792a9ba8a01fbadd4
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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