3-(Pyridin-3-yl)propan-1-amine → HCID 25264819, compound

HRID 1941765Notes

Reaction equation

HRID 1941765 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]2[O:14][CH2:15][C@H:16]([CH3:17])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:20])[C:5]([C:18]#[N:19])=[CH:6]3.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH2:28][CH2:29][NH2:30])[CH:22]=1>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:30][CH2:29][CH2:28][CH2:27][C:23]2[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=2)[C:9]2[O:14][CH2:15][C@H:16]([CH3:17])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:20])[C:5]([C:18]#[N:19])=[CH:6]3

Participants

4

Reactant 2

HCID 135575233-(Pyridin-3-yl)propan-1-amineHCID 58346338(3S)-8-amino-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carbonitrile

Product 1

HCID 25264819HCID 25264819, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5 (30 mg, 0.108 mmol) in 5 ml of DMSO, 29.5 mg (0.216 mmol) of 3-(pyridine-3-yl)propan-1-amine were added. The reaction mixture was heated to 120° C. for 3 h. The DMSO was removed under vacuo and the remaining solid was purified by preparative HPLC to give the title compound as a yellow solid (6.4 mg, 15% yield).

Workup

  1. customThe DMSO was removed under vacuo
  2. customthe remaining solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-8d48d476738b493aa9fdd287fe6c35f9
Source dataset
uspto-grants-2013_03
Patent number
US08389514B2

Reaction notes

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