Diisopropylethylamine → HCID 52936081, compound

HRID 1423027Notes

Reaction equation

HRID 1423027 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[CH:13][N:14]=[N:15][C:16]([C:17]([OH:19])=O)=[C:11]3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[CH3:27][S:28]([C:31]1[CH:36]=[C:35]([CH2:37][NH2:38])[CH:34]=[CH:33][N:32]=1)(=[O:30])=[O:29].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.[Cl-].[NH4+]>[CH3:27][S:28]([C:31]1[CH:36]=[C:35]([CH2:37][NH:38][C:17]([C:16]2[N:15]=[N:14][CH:13]=[C:12]3[N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[N:9]=[CH:10][C:11]=23)=[O:19])[CH:34]=[CH:33][N:32]=1)(=[O:30])=[O:29]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67195560HCID 67195560, compoundHCID 68345602HCID 68345602, compound

Product 1

HCID 52936081HCID 52936081, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-d]pyridazine-4-carboxylic acid (55.0 mg, 0.213 mmol), C-(2-methanesulfonyl-pyridin-4-yl)-methylamine trifluoroacetic acid salt (80.0 mg, 0.266 mmol) and DIPEA (112 μL, 0.644 mmol) in DMF (3.0 mL) is added TBTU (93.0 mg, 0.290 mmol). After 30 minutes, the mixture is diluted with saturated aqueous ammonium chloride (20 mL) and extracted with EtOAc (3×15 mL). The combined organic layers are washed with brine (4×5 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with a gradient of 25-100% EtOAc in hexanes. The resulting solid is triturated with ethyl ether to afford the title compound.

Workup

  1. extractionextracted with EtOAc (3×15 mL)
  2. washThe combined organic layers are washed with brine (4×5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with a gradient of 25-100% EtOAc in hexanes
  8. customThe resulting solid is triturated with ethyl ether

Sources & evidence

ORD record
ord-53853eb25e064b8e86c30d6a2100ee24
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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