Dimethylformamide → HCID 59239182, compound
Reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH2:29][CH3:30])[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].CN(C)C=O.[O:36]1[CH2:41][CH2:40][C:39](=O)[CH2:38][CH2:37]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH2:29][CH3:30])[C:16]3[CH2:22][CH2:21][N:20]([CH:39]4[CH2:40][CH2:41][O:36][CH2:37][CH2:38]4)[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)=[O:5])[CH3:2]Participants
5
Conditions
- Temperature
- 50 °C
Procedure
(S)-1-ethyl-3-(4-(4-(3-ethylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0714 g, 0.174 mmol) in dry N,N-Dimethylformamide (0.850 mL, 11.0 mmol) at 0° C. was added Tetrahydro-4H-pyran-4-one (0.0160 mL, 0.174 mmol). The reaction mixture was stirred at 50° C. for 10 minutes then cooled at 0° C. and added Sodium triacetoxyborohydride (0.0788 g, 0.372 mmol). The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was filtered through a disc filtered, concentrated, chromatographed through silica gel (40 g, 0-10% MeOH in dichloromethane), and purified by HPLC. LC/MS-m/z+495.3 (M+H)+
Workup
- temperaturethen cooled at 0° C.
- temperatureto warm slowly to room temperature
- stirringstirred overnight
- filtrationThe reaction mixture was filtered through a disc
- filtrationfiltered
- concentrationconcentrated
- customchromatographed through silica gel (40 g, 0-10% MeOH in dichloromethane)
- custompurified by HPLC
Sources & evidence
- ORD record
- ord-57a66410986e4005b460dac36998fba5
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163763B2
Reaction notes
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