Acetic Acid → 2-(S)-(4-Fluoro-phenyl)-N-{1-(S)-[(6-methoxy-pyridin-3-ylamino)-methyl]-2-methyl-propyl}-4-morpholin-4-yl-4-oxo-butyramide

HRID 1783875

Reaction equation

HRID 1783875 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:18][C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[C:9]([NH:11][C@H:12]([CH:16]=O)[CH:13]([CH3:15])[CH3:14])=[O:10])=[CH:4][CH:3]=1.[NH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[N:32][CH:33]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:18][C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[C:9]([NH:11][C@H:12]([CH2:16][NH:27][C:28]2[CH:33]=[N:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH:13]([CH3:14])[CH3:15])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 811216-Methoxy-3-pyridinylamineHCID 5003444Sodium cyanoborohydrideHCID 865981972-(S)-(4-Fluoro-phenyl)-N-(1-(S)-formyl-2-methyl-propyl)-4-morpholin-4-yl-4-oxo-butyramide

Product 1

HCID 113634552-(S)-(4-Fluoro-phenyl)-N-{1-(S)-[(6-methoxy-pyridin-3-ylamino)-methyl]-2-methyl-propyl}-4-morpholin-4-yl-4-oxo-butyramide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(S)-(4-Fluoro-phenyl)-N-(1-(S)-formyl-2-methyl-propyl)-4-morpholin-4-yl-4-oxo-butyramide (350 mg, 0.96 mmol, 1.0 eq.) and 5-Amino-2-methoxy-pyridine (240 μL, 1.92 mmol, 2.0 eq.) dissolved in MeOH (2.5 mL) and acetic acid (106 mL, 1.92 mmol, 2.0 eq.) added via syringe at room temperature. Sodium cyanoborohydride (121 mg, 1.92 mmol, 2.0 eq.) added in portion and the reaction monitored the reaction by LC/MS. Upon completion, solvents were evaporated and dissolved in EtOAc (100 mL) washed with brine, dried over MgSO4, filtered and evaporated. Purification by preparative mass-directed HPLC provided the title compound as a white solid after evaporation and lyophilization (2.6 mg, 5.6 □mol, 0.6%). HPLC-MS calcd. for C25H33FN4O4 (M+H+) 473.3, found 473.5.

Workup

  1. customthe reaction by LC/MS
  2. customUpon completion, solvents were evaporated
  3. dissolutiondissolved in EtOAc (100 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by preparative mass-directed HPLC

Sources & evidence

ORD record
ord-950430614803451d89e67ca6730e7c21
Source dataset
uspto-grants-2009_03
Patent number
US07501408B2

Linked notes

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