Triethylamine → HCID 58451253, compound
Reaction equation
[C:1](=[O:12])(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[NH2:13][C:14]1[CH:15]=[C:16]([CH:33]=[CH:34][C:35]=1[F:36])[O:17][C:18]1[N:23]=[C:22]2[S:24][C:25]([NH:27][C:28]([CH:30]3[CH2:32][CH2:31]3)=[O:29])=[N:26][C:21]2=[CH:20][CH:19]=1.C(N(CC)CC)C.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[CH2:50][NH2:51]>O1CCCC1.O.C(OCC)(=O)C>[F:36][C:35]1[CH:34]=[CH:33][C:16]([O:17][C:18]2[N:23]=[C:22]3[S:24][C:25]([NH:27][C:28]([CH:30]4[CH2:32][CH2:31]4)=[O:29])=[N:26][C:21]3=[CH:20][CH:19]=2)=[CH:15][C:14]=1[NH:13][C:1](=[O:12])[NH:51][CH2:50][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][N:44]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a solution of bis(trichloromethyl) carbonate (30 mg, 0.102 mmol) in tetrahydrofuran (2 mL) was added dropwise a suspension of N-[5-(3-amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (100 mg, 0.290 mmol) produced in Example 16(vi) and triethylamine (80 μL, 0.580 mmol) in tetrahydrofuran (2 ml) at 0° C., and the mixture was stirred at 0° C. for 30 min. 1-Pyridin-2-ylmethanamine (40 μL, 0.348 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 3 hr. Ethyl acetate (6 mL) and water (4 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 30 min. The precipitated solid was collected by filtration to give the title compound (81 mg, 58%) as a white solid.
Workup
- stirringthe mixture was stirred at room temperature for 3 hr
- stirringthe mixture was stirred at room temperature for 30 min
- filtrationThe precipitated solid was collected by filtration
Sources & evidence
- ORD record
- ord-ea619c899b7147d2b8f3d90b3e5354cd
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697874B2
Reaction notes
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