Phosgene → HCID 67541363, compound
Reaction equation
[C:1](Cl)(Cl)=[O:2].Cl.[CH3:6][O:7][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH2:14].C(N(CC)CC)C.Cl.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[C:34]([C:36]3[CH:45]=[C:44]4[C:39]([CH2:40][CH2:41][NH:42][CH2:43]4)=[CH:38][CH:37]=3)[N:33]=[C:32]([NH2:46])[N:31]=2)[CH2:26][CH2:25]1>C1(C)C=CC=CC=1.O1CCCC1.C(#N)C>[NH2:46][C:32]1[N:33]=[C:34]([C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][N:42]([C:1]([NH:14][C@@H:9]4[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:8]4[O:7][CH3:6])=[O:2])[CH2:43]3)=[CH:38][CH:37]=2)[CH:35]=[C:30]([N:27]2[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]2)[N:31]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 20% phosgene in toluene [Phosgene:Toluene=1:4 v/v, 24.4 uL, 0.0461 mmol) was added a solution of (cis)-2-methoxycyclohexanamine hydrochloride (5.0 mg, 0.030 mmol) and triethylamine (9.6 uL, 0.069 mmol) in tetrahydrofuran (0.3 mL). The resulted mixture was stirred at r.t. for 2 h., and concentrated. To the residue was added a solution of 4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt (10 mg, 0.02 mmol) and triethylamine (12.8 uL, 0.092 mmol) in acetonitrile (0.3 mL). The reaction mixture was stirred at room temperature for 30 min The mixture was purified by RP-LCMS (pH=10) to afford the desired product. Analytic LCMS (M+H)+: m/z=480.2.
Workup
- concentrationconcentrated
- stirringThe reaction mixture was stirred at room temperature for 30 min The mixture
- customwas purified by RP-LCMS (pH=10)
Sources & evidence
- ORD record
- ord-6174c048b8fa4b5bb72fa6893ed8f4aa
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481732B2
Reaction notes
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