2-Aminocyclohexanol → 1H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-one

HRID 1056024Notes

Reaction equation

HRID 1056024 reaction equation
FC1C(C)=NC2C(N=1)=C([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)C=CC=2.NC1CCCCC1O>>[NH:20]1[C:19]2[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=2[CH:13]=[CH:12]1

Participants

3

Reactant 2

HCID 232862-AminocyclohexanolHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 220385131H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-oneYield 24%

Conditions

Temperature
100 °C

Procedure

Prepared similarly to that described in Example 131 using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 48 mg, 0.162 mmol) and 2-aminocyclohexanol (37.0 mg, 0.324 mmol, TCI America, Portland, Oreg.; mixture of racemic cis- and trans-isomers) and heating at 100° C. for 2 h. Purification by silica gel (100% DCM to 8% MeOH/DCM) provided 2434(2-hydroxycyclohexyl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (24% yield; mixture of racemic cis- and trans-isomers). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37-1.50 (m, 2H) 1.54-1.86 (m, 6H) 2.56 (s, 3H) 2.88 (t, J=6.85 Hz, 2H) 3.44 (td, J=6.75, 2.15 Hz, 2H) 4.08 (br. s., 2H) 4.84 (br. s., 1H) 6.23 (d, J=7.04 Hz, 1H) 6.89 (br. s., 1H) 7.14 (d, J=2.15 Hz, 1H) 7.32 (t, J=7.82 Hz, 1H) 7.56 (d, J=6.85 Hz, 1H) 7.86 (d, J=6.26 Hz, 1H) 11.86 (br. s., 1H). MS (ESI, pos. ion) m/z: 392.3 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 8% MeOH/DCM)

Sources & evidence

ORD record
ord-53ac6c2027c34aa38ba69111ac8512a0
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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