Triethylamine → HCID 57386425, compound
Reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[CH:20]1([CH2:23][NH2:24])[CH2:22][CH2:21]1.[C:25]([CH2:27][C:28]1([N:32]2[CH:36]=[C:35]([C:37]3[CH:42]=[N:41][N:40]4[C:43]([C:46]5[CH:47]=[C:48]([NH:52][C:53]([NH:55][CH2:56][C:57]([F:60])([F:59])[F:58])=[O:54])[CH:49]=[CH:50][CH:51]=5)=[CH:44][N:45]=[C:39]4[CH:38]=3)[CH:34]=[N:33]2)[CH2:31][NH:30][CH2:29]1)#[N:26]>C(Cl)Cl.CN(C)C=O.CO>[C:25]([CH2:27][C:28]1([N:32]2[CH:36]=[C:35]([C:37]3[CH:42]=[N:41][N:40]4[C:43]([C:46]5[CH:51]=[CH:50][CH:49]=[C:48]([NH:52][C:53]([NH:55][CH2:56][C:57]([F:59])([F:60])[F:58])=[O:54])[CH:47]=5)=[CH:44][N:45]=[C:39]4[CH:38]=3)[CH:34]=[N:33]2)[CH2:29][N:30]([C:2]([NH:24][CH2:23][CH:20]2[CH2:22][CH2:21]2)=[O:4])[CH2:31]1)#[N:26]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
Triphosgene (22 mg, 0.074 mmol) was dissolved in DCM (1.0 mL). To the solution was added a solution of triethylamine (12.6 μL, 0.0908 mmol) and cyclopropylmethylamine (6.2 μL, 0.073 mmol) in DCM (1 mL). The mixture was stirred at r.t. for 1 h., the volatiles were removed. To the residue was added a solution of triethylamine (22.9 μL, 0.164 mmol) and N-[3-(7-{1-[3-(cyanomethyl)azetidin-3-yl]-1H-pyrazol-4-yl}imidazo[1,2-b]pyridazin-3-yl)phenyl]-N′-(2,2,2-trifluoroethyl)urea (15 mg, 0.030 mmol) in N,N-dimethylformamide (0.5 mL) and methanol (0.1 mL). The mixture was stirred at r.t. for 1 h., the mixture was purified by RP-LCMS (pH=10) to afford the desired product. LCMS (M+H)+: m/z=593.2.
Workup
- customthe volatiles were removed
- stirringThe mixture was stirred at r.t. for 1 h.
- customthe mixture was purified by RP-LCMS (pH=10)
Sources & evidence
- ORD record
- ord-c99faead90ea4a18b5fcd845d36ce401
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754114B2
Reaction notes
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