2,2,2-Trifluoroethyl trichloromethanesulphonate → HCID 56928840, compound

HRID 510094Notes

Reaction equation

HRID 510094 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:15]=[C:16]([NH2:23])[C:17]3[N:22]=[N:21][NH:20][C:18]=3[N:19]=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:15]=[C:16]([NH2:23])[C:17]3[N:22]=[N:21][N:20]([CH2:52][C:53]([F:56])([F:55])[F:54])[C:18]=3[N:19]=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 178508324HCID 178508324, compound

Product 1

HCID 56928840HCID 56928840, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

150 mg (0.415 mmol) of the compound from example 53 and 113 mg (0.0415 mmol) of BEMP were initially charged in 7 ml of dimethylformamide, and a solution of 117 mg (0.415 mmol) of 2,2,2-trifluoroethyl trichloromethanesulfonate in 2.5 ml of dimethylformamide was added dropwise at 0° C. within 10 min. The mixture was stirred at RT for 16 h. Subsequently, the reaction solution was concentrated under reduced pressure and the residue was purified by means of preparative HPLC (eluent: acetonitrile/water with 0.05% trifluoroacetic acid, gradient 10:90→90:10). 22 mg of the title compound were obtained (11% of theory).

Workup

  1. concentrationSubsequently, the reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by means of preparative HPLC (eluent: acetonitrile/water with 0.05% trifluoroacetic acid, gradient 10:90→90:10)

Sources & evidence

ORD record
ord-6a212df274df442da88306cd6b7aea03
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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