Trifluoroacetic acid → HCID 66735907, compound

HRID 512989Notes

Reaction equation

HRID 512989 reaction equation
[C:1]([O:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:9][C:8]=1[NH2:20])([CH3:4])([CH3:3])[CH3:2].[O:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1.FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>ClCCl>[C:1]([O:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:9][C:8]=1[NH:20][CH:25]1[CH2:26][CH2:27][O:22][CH2:23][CH2:24]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 667359202-Amino-4-(4-methylpiperazin-1-yl) benzoic acid tertbutyl ester

Product 1

HCID 66735907HCID 66735907, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-4-(4-methyl-piperazin-1-yl)-benzoic acid tert-butyl ester (11.5 g, 39.5 mmol) in dichloromethane (340 mL) were added tetrahydro-pyran-4-one (4.5 mL, 49.3 mmol), trifluoroacetic acid (8.2 mL) and tetramethylammonium triacetoxyborohydride (15.57 g, 59.2 mmol). The mixture was stirred at room temperature for 2 hours then washed with 0.5N hydrochloric acid, with 0.5N NaOH and with a saturated solution of NaHCO3. The organic layer was dried over sodium sulfate and evaporated to dryness affording the title compound as a pale yellow solid (13.3 g, 90% yield).

Workup

  1. washthen washed with 0.5N hydrochloric acid, with 0.5N NaOH and with a saturated solution of NaHCO3
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-368db2ab85ea4443bdd1500843e49495
Source dataset
uspto-grants-2015_08
Patent number
US09102662B2

Reaction notes

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