Trifluoroacetic acid → HCID 10480901, compound

HRID 1522914Notes

Reaction equation

HRID 1522914 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([O:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([Cl:32])=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=3)=[O:20])=[CH:16][CH:17]=2)[CH:8]=[CH:9][N:10]=1)=[O:4].C(N(CC)C(C)C)(C)C.[C:42](O)(C(F)(F)F)=[O:43]>C(#N)C.O>[Cl:32][C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:19]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][C:7]3[CH:8]=[CH:9][N:10]=[C:5]([C:3](=[O:4])[NH:2][CH2:1][CH2:42][OH:43])[CH:6]=3)=[CH:13][CH:14]=2)=[O:20])=[CH:27][C:26]=1[C:28]([F:31])([F:29])[F:30]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 216239Sorafenib

Product 1

HCID 10480901HCID 10480901, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

Sorafenib derivative S-6: S-5 (180 mg; 0.30 mmol) was dissolved in acetonitrile (3 ml), and a solution of N,N,N′,N′-tetramethyl-O—(N-succimidyl)uronium tetrafluoroborate (TSTU) (99 mg; 0.32 mmol) in acetonitrile (3 ml) was added, and N,N-diisopropylethylamine (67 μl; 0.37 mmol) was added. HPLC shows complete reaction after 10 min. 0.1% TFA in water (2 ml) is added, and the mixture is purified preparatively HLPC. S-6 is obtained as “off-white” solid substance (163 mg; 0.24 mmol; 78%). MS: M+H=692.1368; calculated for C30H25ClF3N5O9: 692.1371.

Workup

  1. customreaction after 10 min
  2. customthe mixture is purified preparatively HLPC
  3. customS-6 is obtained as “off-white” solid substance (163 mg; 0.24 mmol; 78%)

Sources & evidence

ORD record
ord-cc16fa797ba94812b099ddf5b1c2f26b
Source dataset
uspto-grants-2015_07
Patent number
US09078929B2

Reaction notes

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