Hydrochloric Acid → HCID 59402369, compound
Reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)=[CH:8][CH:9]=2)[CH2:4][N:3]1[C:18](OC(C)(C)C)=O.Cl.O1CCOCC1.[NH2:32][C:33]1[N:38]=[C:37]([Cl:39])[CH:36]=C(Cl)[N:34]=1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C.CCOCC>[Cl:39][C:37]1[N:38]=[C:33]([NH2:34])[N:32]=[C:18]([N:3]2[CH:2]([CH3:1])[CH2:11][C:10]3[C:5](=[CH:6][C:7]([C:12]4[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=4)=[CH:8][CH:9]=3)[CH2:4]2)[CH:36]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
tert-butyl 3-methyl-7-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.320 g, 0.977 mmol) in ethyl acetate (1 mL) was treated with 4.0 M of hydrogen chloride in 1,4-dioxane (1.00 mL, 4.00 mmol) at r.t. for 1 h. The mixture was diluted with ether (5 mL), and was centrifugalized. The solvents were decanted. The residue was dried in-vacuo, and dissolved in tert-butanol (10 mL). To the solution was added 2-amino-4,6-dichloropyrimidine (0.246 g, 1.50 mmol) and N,N-diisopropylethylamine (522 uL, 3.00 mmol). The mixture was heated and stirred at 120° C. overnight. The solvent was removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column with methanol in DCM (0-10%) to give the desired product (303 mg, 87.6%). LCMS (M+H)+: m/z=355.1/357.1.
Workup
- customThe solvents were decanted
- customThe residue was dried in-vacuo
- dissolutiondissolved in tert-butanol (10 mL)
- temperatureThe mixture was heated
- customThe solvent was removed under reduced pressure
- customThe residue was purified by flash chromatography on a silica gel column with methanol in DCM (0-10%)
Sources & evidence
- ORD record
- ord-846e779d95094d619fcb21f13773b62a
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436008B2
Reaction notes
Loading…