Acetic Acid → HCID 17747530, compound

HRID 2099138Notes

Reaction equation

HRID 2099138 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([NH:20][C:21]4[C:26]5[C:27](=[O:35])[N:28]6[C@H:32]([CH2:33][O:34][C:25]=5[CH:24]=[CH:23][CH:22]=4)[CH2:31][CH2:30][CH2:29]6)[C:17]([C:36]([F:39])([F:38])[F:37])=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C=O.[C:42](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O>[CH3:42][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([NH:20][C:21]4[C:26]5[C:27](=[O:35])[N:28]6[C@H:32]([CH2:33][O:34][C:25]=5[CH:24]=[CH:23][CH:22]=4)[CH2:31][CH2:30][CH2:29]6)[C:17]([C:36]([F:37])([F:38])[F:39])=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 577940772-(4-piperazin-1-yl-phenylamino)-4-((S)-4-oxo-2,3,10,10a-tetrahydro-1H.4H-9-oxa-3a-aza-benzo[f]azulen-5-ylamino)-5-trifluoromethyl-pyrimidine

Product 1

HCID 17747530HCID 17747530, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.077 mmol) 2-(4-piperazin-1-yl-phenylamino)-4-((S)-4-oxo-2,3,10,10a-tetrahydro-1H.4H-9-oxa-3a-aza-benzo[f]azulen-5-ylamino)-5-trifluoromethyl-pyrimidine are dissolved in 0.5 mL dimethylformamide and combined with 12 μL (0.154 mmol) formaldehyde and 2 μL (0.039 mmol) acetic acid. 86 mg (0.385 mmol) of sodium triacetoxyborohydride are metered into this mixture and it is stirred for 16 h at ambient temperature. Then the solvent is eliminated in vacuo. The crude product is purified by column chromatography. The carrier material used is C18-RP-silica gel and a gradient is run through which at the starting point consists of 95% water and 5% acetonitrile and at the end point consists of 5% water and 95% acetonitrile. 0.2% Formic acid is added to the two eluants. The suitable fractions are combined with 1 N aqueous hydrochloric acid and freeze-dried.

Workup

  1. customThe crude product is purified by column chromatography
  2. addition0.2% Formic acid is added to the two eluants
  3. customfreeze-dried

Sources & evidence

ORD record
ord-0220ba927bbc46ebac43bd30b098ea69
Source dataset
uspto-grants-2009_08
Patent number
US07569561B2

Reaction notes

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