Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 76072415, compound

HRID 2200089Notes

Reaction equation

HRID 2200089 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:15][C:16]([OH:18])=O)[CH:12]([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.Cl.[F:21][C:22]([F:38])([F:37])[C:23]1[CH:24]=[CH:25][C:26]([N:29]2[CH2:34][CH2:33][O:32][CH:31]([CH2:35][NH2:36])[CH2:30]2)=[N:27][CH:28]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH:12]([CH3:13])[CH3:14])[CH2:15][C:16]([NH:36][CH2:35][CH:31]2[O:32][CH2:33][CH2:34][N:29]([C:26]3[CH:25]=[CH:24][C:23]([C:22]([F:38])([F:37])[F:21])=[CH:28][N:27]=3)[CH2:30]2)=[O:18])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 60827977HCID 60827977, compoundHCID 90159088HCID 90159088, compound

Product 1

HCID 76072415HCID 76072415, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Fluoro-N-isopropylphenylsulfonamido)acetic acid (108 mg, 0.39 mmol), (4-(5-(trifluoromethyl)pyridin-2-yl)morpholin-2-yl)methylamine dihydrochloride (131 mg, 0.39 mmol) and TEA (0.22 mL) were combined in dichloromethane (6 mL). To this stirred solution was added BOP reagent (174 mg, 0.39 mmol). The mixture was stirred at room temperature for 6 h. Solvents were evaporated and the residue was extracted with ethyl acetate and water, washed with sodium bicarbonate solution and dried. Solvents were evaporated. The residue was purified by ISCO flash column chromatography (0% to 100% ethyl acetate in hexanes) to give a white powder (160 mg, 79%). [MH]+=519.0.

Workup

  1. customSolvents were evaporated
  2. extractionthe residue was extracted with ethyl acetate and water
  3. washwashed with sodium bicarbonate solution
  4. customdried
  5. customSolvents were evaporated
  6. customThe residue was purified by ISCO flash column chromatography (0% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d5377ee46fbf4c32870cb7b47f648027
Source dataset
uspto-grants-2016_06
Patent number
US09359337B2

Reaction notes

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