Trifluoroacetic acid → HCID 59437059, compound

HRID 1640988Notes

Reaction equation

HRID 1640988 reaction equation
[NH2:1][C:2]1[CH:49]=[C:48]([N:50]([CH2:52][CH2:53][N:54]([CH3:56])[CH3:55])[CH3:51])[CH:47]=[CH:46][C:3]=1[C:4]([NH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([S:16]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=3)(=[O:18])=[O:17])[CH:14]=2)[N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:8]=1)=[O:5].[O:57]1[CH2:62][CH2:61][C:60](=O)[CH2:59][CH2:58]1.FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>ClCCl>[F:25][C:23]1[CH:24]=[C:19]([S:16]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[NH:9][N:8]=[C:7]3[NH:6][C:4](=[O:5])[C:3]2[CH:46]=[CH:47][C:48]([N:50]([CH2:52][CH2:53][N:54]([CH3:55])[CH3:56])[CH3:51])=[CH:49][C:2]=2[NH:1][CH:60]2[CH2:61][CH2:62][O:57][CH2:58][CH2:59]2)(=[O:18])=[O:17])[CH:20]=[C:21]([F:26])[CH:22]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 121599Tetrahydro-4H-pyran-4-oneHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)2×HCID 66735970HCID 66735970, compound

Product 1

HCID 59437059HCID 59437059, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-N-[5-(3,5-difluoro-benzenesulfonyl)-1-trityl-1H-indazol-3-yl]-4-[(2-dimethylamino-ethyl)-methyl-amino]-benzamide (400 mg, 0.52 mmol) in dichloromethane (5 mL) were added tetrahydro-pyran-4-one (0.071 mL, 0.78 mmol), trifluoroacetic acid (0.108 mL, 1.4 mmol) and tetramethylammonium triacetoxyborohydride (205 mg, 0.78 mmol). The mixture was stirred at room temperature overnight, then additional trifluoroacetic acid (0.8 mL) and tetramethylammonium triacetoxyborohydride (410 mg) were added. After stirring for additional 3 hours at room temperature the mixture was diluted with dichloromethane, washed with saturated solution of sodium hydrogenocarbonate, brine, dried over sodium sulfate and evaporated to dryness. The crude was purified by flash chromatography on silica gel using dichloromethane/methanol/NH4OH 96:4:0.5 as the eluant, affording 175 mg of the title compound as a pale yellow solid.

Workup

  1. stirringAfter stirring for additional 3 hours at room temperature the mixture
  2. washwashed with saturated solution of sodium hydrogenocarbonate, brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-5955929eac3246cf8bfaf358572e9c80
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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