Pyridine → HCID 58010182, compound

HRID 1854469Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH2:22])[N:20]=[C:15]2[CH:14]=1.N1C=CC=CC=1.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1COCC1.C([O-])([O-])=O.[Na+].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:29])[CH3:31])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH:22][C:38](=[O:45])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:20]=[C:15]2[CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.095 g, 0.28 mmol, Example #20, Step G) in THF (5 mL) was treated with pyridine (0.026 ml, 0.33 mmol) and benzoyl chloride (0.033 ml, 0.28 mmol). The mixture was stirred for about 20 min at about 60° C. and cooled to ambient temperature, diluted with aqueous Na2CO3 (15 mL), and extracted with EtOAc (20 mL). The organic solution was dried over anhydrous MgSO4, filtered, and concentrated to give N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)benzamide (0.118 g, 100%): LC/MS (Table 2, Method d) Rt=1.64 min; MS m/z: 542 (M+H)+.

Workup

temperaturecooled to ambient temperature
extractionextracted with EtOAc (20 mL)
dry with materialThe organic solution was dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-13bbaaa8f65642e780d64209e1d45072
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962629B2

Reaction notes

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