1-Boc-3,3-dimethylpiperazine → HCID 89784004, compound

HRID 1056039Notes

Reaction equation

HRID 1056039 reaction equation
F[C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.[CH3:22][C:23]1([CH3:36])[NH:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]1>>[CH3:22][C:23]1([CH3:36])[N:28]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[C:9]([C:12]4[NH:20][C:19]5[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=5[CH:13]=4)[CH:8]=[CH:7][CH:6]=3)[N:11]=2)[CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]1

Participants

3

Reactant 2

HCID 227103871-Boc-3,3-dimethylpiperazineHCID 897843702-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89784004HCID 89784004, compoundYield 16%

Conditions

Temperature
120 °C

Procedure

Prepared similarly to that described in Example 210 using 2-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 210i; 100 mg, 0.354 mmol) and tert-butyl 3,3-dimethylpiperazine-1-carboxylate (152 mg, 0.709 mmol), heating at 120° C. for 1 d. Purification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA) provided tert-butyl 3,3-dimethyl-4-(8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)piperazine-1-carboxylate (16% yield). MS (ESI, pos. ion) m/z: 477.2 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA)

Sources & evidence

ORD record
ord-124628fd53c5479580ee7e9c5c5c3c5c
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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