Sodium Iodide → HCID 136983916, compound

HRID 1507498Notes

Reaction equation

HRID 1507498 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[C:9]([NH:22][C@@H:23]3[CH2:28][CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]3)=[N:10][C:11]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[N:12][C:13]=2[O:14]C)=[N:6][CH:7]=1.[Na+].[I-].[Si](Cl)(C)(C)C>CC#N>[F:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[C:13](=[O:14])[NH:12][C:11]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[N:10][C:9]=2[NH:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 89545209HCID 89545209, compound

Product 1

HCID 136983916HCID 136983916, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (R)-tert-butyl 3-((5-fluoro-6′-methoxy-2′-morpholino-[2,5′-bipyrimidin]-4′-yl)amino)piperidine-1-carboxylate (0.025 g, 0.051 mmol) in MeCN (1 mL) was added NaI (0.011 g, 0.077 mmol) followed by TMS-Cl (9.79 μl, 0.077 mmol). The reaction was stirred at room temperature for 15 min. then heated to 50° C. for 3 h. The solvent was removed in vacuo and the residue was purified via semi-preparative HPLC to afford the desired product as a white solid. MS (m/z)=376 (M+H). IRAK4 IC50=220 nM

Workup

  1. temperaturethen heated to 50° C. for 3 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified via semi-preparative HPLC

Sources & evidence

ORD record
ord-6be897cc4e7c4e22818bd1ad50378a02
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

Loading…