Trifluoroacetic acid → HCID 68424670, compound

HRID 1891028Notes

Reaction equation

HRID 1891028 reaction equation
C(OC([N:8]1[CH2:20][C:19]2[S:18][C:17]3[N:16]=[CH:15][N:14]=[C:13]([NH:21][CH:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:23][OH:24])[C:12]=3[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>ClCCl>[C:25]1([CH:22]([NH:21][C:13]2[C:12]3[C:11]4[CH2:10][CH2:9][NH:8][CH2:20][C:19]=4[S:18][C:17]=3[N:16]=[CH:15][N:14]=2)[CH2:23][OH:24])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68422822HCID 68422822, compound

Product 1

HCID 68424670HCID 68424670, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(2-hydroxy-1-phenyl-ethylamino)-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluorene-7-carboxylic acid tert-butyl ester (0.6 g) in dichloromethane (2 mL) at room temperature was added TFA (1 mL). The reaction mixture was stirred for 4 h, then neutralized by slow addition of sodium bicarbonate solution. The precipitate formed was collected by filtration and washed with water then dichloromethane to give the title compound (0.350 g, 76%). 1H NMR (400 MHz, CDCl3): δ 8.28 (s, 1H), 7.26-7.38 (m, 5H), 6.04 (d, 1H, J=6.4 Hz), 5.38 (d, 1H, J=4.8 Hz), 4.01 (d, 2H, J=7.6 Hz), 3.99 (d, 2H, J=3.2 Hz), 3.20 (t, 2H, J=4.4 Hz), 2.84-3.04 (m, 2H). LC-MS (ESI) m/z 327.1 (M+H).

Workup

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-4507601b6d8b48f1a7b321dc1c2e9e37
Source dataset
uspto-grants-2013_08
Patent number
US08507502B2

Reaction notes

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