Toluene → HCID 59496652, compound
Reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.Cl.[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[C:24]([C:26]3[CH:35]=[C:34]4[C:29]([CH2:30][CH2:31][NH:32][CH2:33]4)=[CH:28][CH:27]=3)[N:23]=[C:22]([NH2:36])[N:21]=2)[CH2:16][CH2:15]1.C(N(CC)CC)C.[CH3:44][C:45]1[C:46]([N:51]2[CH2:56][CH2:55][CH:54]([NH2:57])[CH2:53][CH2:52]2)=[N:47][CH:48]=[CH:49][CH:50]=1>C(#N)C>[NH2:36][C:22]1[N:23]=[C:24]([C:26]2[CH:35]=[C:34]3[C:29]([CH2:30][CH2:31][N:32]([C:1]([NH:57][CH:54]4[CH2:55][CH2:56][N:51]([C:46]5[C:45]([CH3:44])=[CH:50][CH:49]=[CH:48][N:47]=5)[CH2:52][CH2:53]4)=[O:2])[CH2:33]3)=[CH:28][CH:27]=2)[CH:25]=[C:20]([N:17]2[CH2:16][CH2:15][N:14]([CH3:13])[CH2:19][CH2:18]2)[N:21]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 20% phosgene in toluene (Phosgene:Toluene=1:4, 20.1 uL, 0.0380 mmol) was added a solution of 4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt (15 mg, 0.034 mmol) and triethylamine (14.4 uL, 0.104 mmol) in acetonitrile (0.5 mL). The resulting mixture was stirred for 10 min A mixture of 1-(3-methylpyridin-2-yl)piperidin-4-amine (9.8 mg, 0.051 mmol) (Alfa Aesar, Cat. #H50779) and triethylamine (14 uL, 0.10 mmol) in acetonitrile (0.3 mL) was added to above mixture. The reaction mixture was stirred at r.t. for 30 min., and then purified by RP-LCMS (pH=10) to afford the desired product. Analytic LCMS (M+H)+: m/z=542.3.
Workup
- additionwas added to above mixture
- stirringThe reaction mixture was stirred at r.t. for 30 min.
- custompurified by RP-LCMS (pH=10)
Sources & evidence
- ORD record
- ord-41751b943de4465ca607fa23c39fa331
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481732B2
Reaction notes
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