Ammonium Chloride → N-{2-[(2,3-Difluorobenzyl)thio]-6-[(1R)-2-hydroxy-1-methylethoxy]pyrimidin-4-yl}-9-methyl-3,9-diazabicyclo[4.2.1]nonane-3-sulfonamide

HRID 1024960Notes

Reaction equation

HRID 1024960 reaction equation
[F:1][C:2]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][S:5][C:6]1[N:11]=[C:10]([O:12][C@H:13]([CH3:19])[C:14](OCC)=[O:15])[CH:9]=[C:8]([NH:20][S:21]([N:24]2[CH2:31][CH2:30][CH:29]3[N:32]([CH3:33])[CH:26]([CH2:27][CH2:28]3)[CH2:25]2)(=[O:23])=[O:22])[N:7]=1.[Li+].[BH4-].[NH4+].[Cl-]>C1COCC1>[F:1][C:2]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][S:5][C:6]1[N:7]=[C:8]([NH:20][S:21]([N:24]2[CH2:31][CH2:30][CH:29]3[N:32]([CH3:33])[CH:26]([CH2:27][CH2:28]3)[CH2:25]2)(=[O:22])=[O:23])[CH:9]=[C:10]([O:12][C@H:13]([CH3:19])[CH2:14][OH:15])[N:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 53628383ethyl (2R)-2-[(2-[(2,3-difluorobenzyl)thio]-6-{[(9-methyl-3,9-diazabicyclo[4.2.1]non-3-yl)sulfonyl]amino}pyrimidin-4-yl)oxy]propanoate

Product 1

HCID 53628382N-{2-[(2,3-Difluorobenzyl)thio]-6-[(1R)-2-hydroxy-1-methylethoxy]pyrimidin-4-yl}-9-methyl-3,9-diazabicyclo[4.2.1]nonane-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl (2R)-2-[(2-[(2,3-difluorobenzyl)thio]-6-{[(9-methyl-3,9-diazabicyclo[4.2.1]non-3-yl)sulfonyl]amino}pyrimidin-4-yl)oxy]propanoate (the product from step i), 0.35 g) in THF (10 ml) was added 2M LiBH4 in THF (0.6 ml). The reaction was then stirred for 18 h at room temperature. Saturated NH4Cl (150 ml) was then added to the reaction mixture which was extracted with DCM (3×150 ml). Organics were combined, dried (MgSO4) and reduced in vacuo and the resulting residue was purified by prep HPLC to give the title compound as a white solid. Yield 20 mg

Workup

  1. extractionwas extracted with DCM (3×150 ml)
  2. dry with materialdried (MgSO4)
  3. customthe resulting residue was purified by prep HPLC

Sources & evidence

ORD record
ord-ccff65ec3156450eb06d1e0217b8e86c
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

Loading…