Sodium Hydroxide → HCID 44819462, compound

HRID 337188Notes

Reaction equation

HRID 337188 reaction equation
[OH:1][C@@H:2]1[C@H:7]([OH:8])[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][C:19]=1[F:25].[BH4-].[Na+].[OH-].[Na+]>[Pd](Cl)Cl.C1COCC1.O>[OH:1][C@@H:2]1[C@H:7]([OH:8])[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:25]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 45107726HCID 45107726, compound2×

Product 1

HCID 44819462HCID 44819462, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A sealed tube was charged with (N-[(1R,2S,3R)-2,3-dihydroxycyclohexyl]-3-[(2-fluoro-4-iodophenyl)amino]isonicotinamide) (8) (42 mg, 0.09 mmol), Sodium borohydride (34 mg, 0.89 mmol), palladium dichloride (7.9 mg, 0.04 mmol), sodium hydroxide (17.8 mg, 0.45 mmol), THF-Water (1:1, 3 ml). The mixture was stirred at room temperature for 2 days. The mixture was filtered and the filtrate was concentrated. The resulting residue was subjected to flash chromatography to obtain the product. LC/MS [Method A: rt: 0.43 min; m/z: 346 (M+1)].

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto obtain the product
  4. customLC/MS [Method A: rt: 0.43 min; m/z: 346 (M+1)]

Sources & evidence

ORD record
ord-e60f548137304a8bae908730dc51d237
Source dataset
uspto-grants-2014_11
Patent number
US08889719B2

Reaction notes

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