2,2,2-Trifluoroethyl trichloromethanesulphonate → HCID 66614606, compound

HRID 510083Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:28])[NH:6]2.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.ClC(Cl)(Cl)S(O[CH2:53][C:54]([F:57])([F:56])[F:55])(=O)=O>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:28])[N:6]2[CH2:53][C:54]([F:57])([F:56])[F:55]

Participants

Conditions

Temperature: 0 °C

Procedure

100 mg (0.266 mmol) of the compound from example 33 and 73 mg (0.266 mmol) of BEMP were initially charged in 9 ml of dimethylformamide, and a solution of 75 mg (0.266 mmol) of 2,2,2-trifluoroethyl trichloromethanesulfonate in 1 ml of dimethylformamide was added dropwise at 0° C. within 10 min. The mixture was stirred at 0° C. for 20 min. Subsequently, the reaction solution was concentrated under reduced pressure and the residue was purified by means of preparative HPLC (eluent: methanol/water, gradient 30:70→90:10). 60 mg of the title compound were obtained (47% of theory).

Workup

concentrationSubsequently, the reaction solution was concentrated under reduced pressure
customthe residue was purified by means of preparative HPLC (eluent: methanol/water, gradient 30:70→90:10)

Sources & evidence

ORD record: ord-59365c59325c481da489aba023d0cda3
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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