Iodoethane → (R)-7-(4-(1-ethylpiperidin-4-yl)phenyl)-N-((4-(methylsulfonyl)morpholin-2-yl)methyl)pyrido[4,3-b]pyrazin-5-amine

HRID 57646Notes

Reaction equation

[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][O:8][C@H:7]([CH2:11][NH:12][C:13]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][N:21]=3)[CH:16]=[C:15]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[CH:25][CH:24]=3)[N:14]=2)[CH2:6]1)(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].I[CH2:42][CH3:43]>CN(C=O)C.CC(=O)OCC>[CH2:42]([N:32]1[CH2:33][CH2:34][CH:29]([C:26]2[CH:25]=[CH:24][C:23]([C:15]3[N:14]=[C:13]([NH:12][CH2:11][C@H:7]4[O:8][CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:6]4)[C:22]4[C:17](=[N:18][CH:19]=[CH:20][N:21]=4)[CH:16]=3)=[CH:28][CH:27]=2)[CH2:30][CH2:31]1)[CH3:43]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (R)—N-((4-(methylsulfonyl)morpholin-2-yl)methyl)-7-(4-(piperidin-4-yl)phenyl)pyrido[4,3-b]pyrazin-5-amine in (39.5 mg, 0.082 mmol) in DMF (5 mL) was added K2CO3 (22.6 mg, 0.164 mmol) and iodoethane (25.5 mg, 0.164 mmol) at room temperature. The reaction was stirred at 100° C. for 18 hours. After that, the reaction was dissolved in 50 mL of EA, washed with H2O (25 mL) and brine (25 mL), dried over Na2SO4 and concentrated, purified on TLC (CH2Cl2:MeOH=20:1) to give yellow solid. MS (m/z): 511 (M+H)+

Workup

washwashed with H2O (25 mL) and brine (25 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
custompurified on TLC (CH2Cl2:MeOH=20:1)
customto give yellow solid

Sources & evidence

ORD record: ord-94db86058942461489343301fbea363f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434726B2

Reaction notes

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