Trifluoroacetic acid → HCID 22139438, compound

HRID 1825803Notes

Reaction equation

HRID 1825803 reaction equation
C(OC([N:8]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([C:22]3[O:23][C:24]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:25][C:26](=[O:28])[CH:27]=3)[C:16]=2[S:15][C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:29]1([C:24]2[O:23][C:22]([C:17]3[C:16]4[S:15][C:14]5[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=5)[NH:8][C:21]=4[CH:20]=[CH:19][CH:18]=3)=[CH:27][C:26](=[O:28])[CH:25]=2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 235745714-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-phenothiazine-10-carboxylic Acid tert-Butyl Ester

Product 1

HCID 22139438HCID 22139438, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-phenothiazine-10-carboxylic acid tert-butyl ester (3.65 g, 7.63 mmol), in CH2Cl2 (30 ml) was added trifluoroacetic acid in a single portion. The mixture was stirred at room temperature for 20 hours whereupon the reaction was concentrated in vacuo to give a thick syrup that was basified in a dropwise fashion with saturated NaHCO3 (40 ml). The dark green mixture was then stirred at room temperature for 18 hours. The mixture was filtered and the filtrant retained, washed with water and dried to give the title compound as a dark green solid (2.89 g, 83.74% over 3 steps) m/z (LC-MS, ESP): 479 [M+H]+, R/T=4.05 mins

Workup

  1. concentrationwas concentrated in vacuo
  2. customto give a thick syrup that
  3. stirringThe dark green mixture was then stirred at room temperature for 18 hours
  4. filtrationThe mixture was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-d98630fe4d6242f2b3ad58775e3bb7b1
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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