Morpholine → HCID 11539686, compound

HRID 419005Notes

Reaction equation

HRID 419005 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:18](O)=[O:19])=[N:14][CH:15]=[CH:16][N:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:18]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:19])=[N:14][CH:15]=[CH:16][N:17]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:21]([F:24])([F:22])[F:23]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 57942381HCID 57942381, compound

Product 1

HCID 11539686HCID 11539686, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 20 mg of 3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyrazine-2-carboxylic acid, 10 mg of morpholine and 20 μl of DIEA in 1.5 mL of CH2Cl2 was added 32 μL of 1-propanephosphonic acid cyclic anhydride (50% in ethyl acetate). After 3-4 hours the reaction mixture was directly purified via flash column (65% ethyl acetate in hexane) to afford 14 mg of 4-chloro-N-[3-(morpholine-4-carbonyl)-pyrazin-2-yl]-3-trifluoromethyl-benzenesulfonamide as a white powder. MS: (M+H)/z=451.0.

Workup

  1. customAfter 3-4 hours the reaction mixture was directly purified via flash column (65% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-91277dc686c34351b7ea156259d61d27
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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