Methanol → HCID 59605953, compound
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH:10]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)([CH3:9])[CH3:8])[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.C1COCC1.CO.Br[CH2:45][C:46]1[N:47]([CH3:71])[C:48]2[C:53]([N:54]=1)=[C:52]([N:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1)[N:51]=[C:50]([N:61]1[C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][C:64]=3[N:63]=[C:62]1[CH3:70])[N:49]=2>>[CH3:71][N:47]1[C:46]([CH2:45][N:1]2[CH2:2][CH2:3][CH:4]([C:7]([NH2:10])([CH3:8])[CH3:9])[CH2:5][CH2:6]2)=[N:54][C:53]2[C:48]1=[N:49][C:50]([N:61]1[C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][C:64]=3[N:63]=[C:62]1[CH3:70])=[N:51][C:52]=2[N:55]1[CH2:56][CH2:57][O:58][CH2:59][CH2:60]1Participants
Procedure
According to General Procedure E, [(9H-fluoren-9-yl)methyl 2-(piperidin-4-yl)propan-2-ylcarbamate (0.0923 g, 0.253 mmol) and N,N-diisopropylethylamine (0.265 mL, 0.00152 mol) were mixed in THF (0.7 mL, 0.008 mol) and Methanol (0.7 mL, 0.02 mol) at room temperature, and 4-(8-(bromomethyl)-9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-9H-purin-6-yl)morpholine (0.112 g, 0.253 mmol) was added. The reaction was stirred overnight. The reaction mixture was concentrated to dryness. The crude residue was dissolved in N,N-Dimethylformamide (2.0 mL) and Piperidine (0.200 mL) was added. The mixture was stirred overnight at room temperature. The reaction mixture was concentrated. The crude was purified by reverse phase HPLC to give 383 (45.5 mg, 35.7%). [M+H]+=504.3.
Workup
- concentrationThe reaction mixture was concentrated to dryness
- dissolutionThe crude residue was dissolved in N,N-Dimethylformamide (2.0 mL)
- additionPiperidine (0.200 mL) was added
- stirringThe mixture was stirred overnight at room temperature
- concentrationThe reaction mixture was concentrated
- customThe crude was purified by reverse phase HPLC
Sources & evidence
- ORD record
- ord-0aeab7ed96d6429181e764c308433dbe
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394796B2
Reaction notes
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