Diisopropylethylamine → HCID 90422300, compound
Reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:23][C:24]1[CH:25]=[CH:26][C:27]([N:33]2[N:37]=[CH:36][CH:35]=[N:34]2)=[C:28]([CH:32]=1)[C:29]([OH:31])=O.CCN(C(C)C)C(C)C.Cl.[NH:48]1[CH2:51][CH2:50][C@H:49]1[C:52]([O:54][CH3:55])=[O:53]>C(Cl)Cl.O>[CH3:55][O:54][C:52]([C@@H:49]1[CH2:50][CH2:51][N:48]1[C:29](=[O:31])[C:28]1[CH:32]=[C:24]([CH3:23])[CH:25]=[CH:26][C:27]=1[N:33]1[N:37]=[CH:36][CH:35]=[N:34]1)=[O:53]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
TBTU (4.93 g, 15.4 mmol) was added to a rt solution of 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid A-1-2 (2.40 mg, 11.8 mmol) and DIPEA (8.09 mL, 47.2 mmol) in DCM (24 mL) and after stirring for 15 min, (S)-methyl azetidine-2-carboxylate HCl (2.03 g, 13 mmol) was added and the resulting mixture was stirred at rt for 1 h. The rxn mixture was diluted with DCM and water, the layers were separated and the aq. layer was extracted with DCM (1×). The combined org. extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude was purified by FC (EtOAc/hept 5:1) to obtain the title compound A-2-1 as a white solid. LC-MS A: tR=0.70 min; [M+H]+=301.18.
Workup
- customthe layers were separated
- extractionthe aq. layer was extracted with DCM (1×)
- washextracts were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude was purified by FC (EtOAc/hept 5:1)
Sources & evidence
- ORD record
- ord-516c08ac69c249d6b6b149a002fc5337
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403813B2
Reaction notes
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