tert-Butyl mercaptan → HCID 89784499, compound

HRID 1056044Notes

Reaction equation

HRID 1056044 reaction equation
F[C:2]1[C:3]([CH3:22])=[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.[CH3:23][C:24]([SH:27])([CH3:26])[CH3:25]>>[C:24]([S:27][C:2]1[C:3]([CH3:22])=[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)([CH3:26])([CH3:25])[CH3:23]

Participants

3

Reactant 2

HCID 6387tert-Butyl mercaptanHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89784499HCID 89784499, compoundYield 26%

Conditions

Temperature
100 °C

Procedure

Prepared similarly to that described in Example 127 using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 210i; 74 mg, 0.250 mmol) and 2-methylpropane-2-thiol (67.6 mg, 0.749 mmol; Acros, Geel, Belgium), heating at 100° C. for 7 h. Purification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA) provided 2-(3-(tert-butylthio)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (26% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.62 (s, 9H) 2.59 (s, 3H) 2.83 (t, J=6.85 Hz, 2H) 3.43 (td, J=6.80, 2.25 Hz, 2H) 6.93 (d, J=2.15 Hz, 2H) 7.63 (t, J=7.63 Hz, 1H) 7.80-7.88 (m, 2H) 11.50 (br. s., 1H). MS (ESI, pos. ion) m/z: 367.1 (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-4b867c9864824b6f80fd3c4d2d4ce7b7
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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