Trifluoroacetic acid → HCID 59853039, compound

HRID 2374043Notes

Reaction equation

HRID 2374043 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[C:11]([CH:13]([OH:28])[C:14]2[CH:19]=[CH:18][C:17]([NH:20]C(=O)OC(C)(C)C)=[CH:16][CH:15]=2)[CH:10]=[CH:9][N:8]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH:13]([C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:29])[CH:12]=2)[OH:28])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052Triethylsilane2×HCID 59853024HCID 59853024, compound

Product 1

HCID 59853039HCID 59853039, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of tert-butyl 4-((2-(3-(dimethylamino)propylamino)pyridin-4-yl)(hydroxy)methyl)phenylcarbamate (16 mg, 0.04 mmol) in 1 mL of DCM were added Et3SiH (0.1 mL)/TFA in DCM (10%, 0.2 mL). The mixture was stirred for 1 hr and no reaction was detected by LC-MS. Another 0.1 mL of Et3SiH and 0.8 mL of TFA in DCM (10%) were added and the mixture was stirred for 2 h. The solvent was removed and was purified by solid extraction (Waters Oasis®MCX extraction cartridge) to give (4-aminophenyl)(2-(3-(dimethylamino)propylamino)pyridin-4-yl)methanol (6.0 mg, 50% yield). MS(ESI+): m/z 301.40 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. customThe solvent was removed
  3. customwas purified by solid extraction (Waters Oasis®MCX extraction cartridge)

Sources & evidence

ORD record
ord-e793f55b85e642e48826b7877b04f208
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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