HCID 118274946, compound → HCID 118274944, compound

HRID 1777840Notes

Reaction equation

HRID 1777840 reaction equation
[NH2:1][C@H:2]([C:6]1[N:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:7]=1[C:8](OCC)=[O:9])[CH:3]([CH3:5])[CH3:4]>C1(C)C=CC=CC=1>[Cl:17][C:14]1[CH:13]=[C:7]2[C:8](=[O:9])[NH:1][C@@H:2]([CH:3]([CH3:5])[CH3:4])[C:6]2=[N:16][CH:15]=1

Participants

3

Reactant 1

HCID 118274946HCID 118274946, compound

Product 1

HCID 118274944HCID 118274944, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl(S)-2-(1-amino-2-methylpropyl)-5-chloronicotinate (282 mg, 1.10 mmol) was heated in toluene (5 mL) at 100° C. for 15 h. The solvent was removed in vacuo to yield crude (S)-3-chloro-7-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, which was carried forward without further purification. LCMS: tR=0.73 min in in 1 min chromatography, MS (ESI) m/z 211.2 [M+H]+. 1H NMR (CD3OD, 400 MHz): δ 8.70 (d, J=2.8 Hz, 1H), 8.07 (d, J=2.0 Hz, 1H), 6.75 (broad s, 1H), 4.55 (dd, J=1.2 Hz, 3.6 Hz, 1H), 2.49-2.41 (m, 1H), 1.23 (d, J=7.2 Hz, 3H), 0.74 (d, J=6.8 Hz, 3H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5ddad0b2a9eb40e7922de7c63c49e215
Source dataset
uspto-grants-2016_02
Patent number
US09266886B2

Reaction notes

Loading…