2,2,2-Trifluoroethyl trichloromethanesulphonate → HCID 66614119, compound

HRID 510095Notes

Reaction equation

HRID 510095 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[CH:19][NH:20]3)=[C:16]([NH2:23])[N:15]=2)=[N:6]1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.ClC(Cl)(Cl)S(O[CH2:52][C:53]([F:56])([F:55])[F:54])(=O)=O>CN(C)C=O>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[CH:19][N:20]3[CH2:52][C:53]([F:56])([F:55])[F:54])=[C:16]([NH2:23])[N:15]=2)=[N:6]1

Participants

5

Reactant 3

HCID 900272,2,2-Trifluoroethyl trichloromethanesulphonateHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 178508323HCID 178508323, compound

Product 1

HCID 66614119HCID 66614119, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

100 mg (0.278 mmol) of the compound from example 58 and 76 mg (0.278 mmol) of BEMP were initially charged in 3 ml of dimethylformamide, a solution of 78 mg (0.266 mmol) of 2,2,2-trifluoroethyl trichloromethanesulfonate in 2 ml of dimethylformamide was added dropwise at 0° C. within 10 min and the mixture was stirred at RT for 20 min The product was precipitated by adding water, filtered off with suction and purified by means of preparative HPLC (eluent: acetonitrile/water with 0.05% trifluoroacetic acid, gradient 20:80→50:50). 53 mg of the title compound were obtained (43% of theory).

Workup

  1. customwas precipitated
  2. additionby adding water
  3. filtrationfiltered off with suction
  4. custompurified by means of preparative HPLC (eluent: acetonitrile/water with 0.05% trifluoroacetic acid, gradient 20:80→50:50)

Sources & evidence

ORD record
ord-ff5868d529ce4bd59ada21b43155b1b4
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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