Formaldehyde → HCID 89783587, compound

HRID 1056153Notes

Reaction equation

[C:1]([NH:5][C:6]1[C:7]([CH3:26])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:24][C:23]3[CH2:22][CH2:21][NH:20][C:19](=[O:25])[C:18]=3[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].[C:27]([O-])([O-])=[O:28].[K+].[K+].C=O.CCOC(C)=O.CCO>C1COCC1>[C:1]([NH:5][C:6]1[C:7]([CH3:26])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:24][C:23]3[CH2:22][CH2:21][N:20]([CH2:27][OH:28])[C:19](=[O:25])[C:18]=3[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (193) (0.2 g, 0.57 mmol), K2CO3 (0.16 g, 1.14 mmol), and formaldehyde (Sigma-Aldrich) (0.46 mL of 37% wt. in water, 5.72 mmol) in THF (5.72 mL) were combined and stirred at 50° C. overnight. The reaction mixture was directly loaded onto a biotage and purified three times (0-100% EtOAc:EtOH (3:1)/hexane; 0-40% then 40% EtOAc:EtOH (3:1)/hexanes; then 0-20% then 20% EtOAc:EtOH (3:1)/hexanes) to yield the title compound (6 mg, 3% yield). 1H NMR (300 MHz, CDCl3) d ppm 1.49-1.75 (m, 23H) 2.56 (s, 3H) 2.95-3.10 (m, 2H) 3.20-3.34 (m, 1H) 3.74-3.91 (m, 2H) 4.79-4.92 (m, 1H) 4.98-5.08 (m, 2H) 7.01-7.14 (m, 1H) 7.31-7.46 (m, 1H) 7.59-7.72 (m, 1H) 7.89-8.03 (m, 1H) 12.51-12.65 (m, 1H). m/z (ES, +ve) 380.1 (M+H)+.

Workup

custompurified three times (0-100% EtOAc:EtOH (3:1)/hexane

Sources & evidence

ORD record: ord-3b1ac731266e45fe9eb72725a54233c6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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