Diisopropylethylamine → 8-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine
Reaction equation
Cl.NO.C([N:7](CC)C(C)C)(C)C.C(OC(=O)[NH:17][C:18](=S)[NH:19][C:20]1[C:25]([Br:26])=[CH:24][CH:23]=[CH:22][N:21]=1)C>CO.C(O)C>[Br:26][C:25]1[C:20]2[N:21]([N:7]=[C:18]([NH2:17])[N:19]=2)[CH:22]=[CH:23][CH:24]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of hydroxylamine hydrochloride (0.10 kg, 1.4 mol, 5.0 equiv) and N,N-diisopropylethylamine (112 g, 0.867 mol, 3.00 eq) in 1:1 methanol/ethanol (1.5 L) was added ethyl[(3-bromopyridin-2-yl)carbamothioyl]carbamate (88 g, 0.29 mmol, 1 equiv) in one portion at room temperature. After 2 h, the reaction mixture was warmed to 60° C. for overnight. The reaction mixture was concentrated in vacuo, and water was added to the resulting residue. The solids were filtered and rinsed sequentially with 4:1 methanol/diethyl ether and diethyl ether to provide product as an off-white solid (25 g, 40%). LCMS (ESI) m/z: 212.8; 1H NMR (400 MHz, DMSO-d6) δ: 8.55 (m 1 H), 7.70 (m, 1 H), 6.75 (m, 1 H), 6.20 (br s, 2 H).
Workup
- concentrationThe reaction mixture was concentrated in vacuo, and water
- additionwas added to the resulting residue
- filtrationThe solids were filtered
- washrinsed sequentially with 4:1 methanol/diethyl ether and diethyl ether
Sources & evidence
- ORD record
- ord-bebc42d331354df5ba28fd4a00040792
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609687B2
Reaction notes
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