Pyridine → HCID 58459378, compound

HRID 2036645Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[C:13]([C:17]([O-:19])=[O:18])=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[N:6][CH:7]=1.[I-].[Li+].[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[NH2:22][C:27]1[C:4]([C:5]#[N:6])=[C:23]([NH:10][C@H:9]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([OH:19])=[O:18])[N:12]3[C:8]=2[C:4]2[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH3:8])[CH:24]=[CH:25][CH:26]=1

Participants

Reactant 3

HCID 1049Pyridine

HCID 66321Lithium iodide

HCID 86658170HCID 86658170, compound

Product 1

HCID 58459378HCID 58459378, compound

Procedure

A solution of methyl 2-((1S)-1-(6-amino-5-cyano-4-pyrimidinyl)amino)ethyl)-3-(5-fluoro-3-pyridinyl)imidazo[1,2-a]pyridine-5-carboxylate (0.060 g, 0.139 mmol) and lithium iodide (0.056 g, 0.416 mmol) in pyridine (0.73 mL) was stirred at 100° C. for 6 h. Volatiles were removed under reduced pressure to afford (S)-2-(1-((3-amino-2-cyanophenyl)amino)ethyl)-3-(5-fluoropyridin-3-yl)imidazo[1,2-a]pyridine-5-carboxylic acid as a dark residue. LC-MS (ESI) m/z 419.1 [M+H]+.

Workup

customVolatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-c699fec8ceb14d3f86ce9b1823947fc0
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575183B2

Reaction notes

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