Diisopropylethylamine → HCID 44476576, compound
Reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[N:10]=[CH:9][C:8]([C:11]([OH:13])=O)=[CH:7][CH:6]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.O[NH:50][C:51]([C:53]1[C:54]2[CH:55]=[CH:56][N:57]=[CH:58][C:59]=2[CH:60]=[CH:61][CH:62]=1)=[NH:52]>CN(C=O)C>[F:14][C:2]([F:1])([F:15])[CH2:3][O:4][C:5]1[N:10]=[CH:9][C:8]([C:11]2[O:13][N:52]=[C:51]([C:53]3[CH:62]=[CH:61][CH:60]=[C:59]4[C:54]=3[CH:55]=[CH:56][N:57]=[CH:58]4)[N:50]=2)=[CH:7][CH:6]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
6-[(2,2,2-Trifluoroethyl)oxy]-3-pyridinecarboxylic acid (Fluorochem; 130 mg, 0.642 mmol) was stirred in DMF (1 ml) with HATU (244 mg, 0.642 mmol) and DIPEA (0.28 ml, 1.605 mmol) at room temperature for 30 mins before adding a solution of N-hydroxy-5-isoquinolinecarboximidamide (D1, 100 mg, 0.535 mmol) in DMF (1 ml). The resulting mixture was heated to 120° C. for 30 mins in a Biotage Initiator microwave. The solvent was removed under vacuum, and the residue was purified by column chromatography on silica, eluting with 0-60% ethyl acetate in cyclohexane. The relevant fractions were combined and concentrated under vacuum to give the title compound as a white solid (28 mg).
Workup
- customThe solvent was removed under vacuum
- customthe residue was purified by column chromatography on silica
- washeluting with 0-60% ethyl acetate in cyclohexane
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-98b375d79e3b406e8ceb335a330395c0
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329730B2
Reaction notes
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