Sodium borohydride → HCID 59593284, compound

HRID 1754676Notes

Reaction equation

HRID 1754676 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=[C:4]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[N:3]=1.[BH4-].[Na+]>CO>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][NH:19][C:4]2[N:3]=[C:2]([Cl:1])[C:7]([CH:8]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=4)[NH:12][CH:11]=3)[OH:9])=[CH:6][CH:5]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59593312HCID 59593312, compound

Product 1

HCID 59593284HCID 59593284, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To [2-Chloro-6-(4-chloro-benzylamino)-pyridin-3-yl]-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (P-0048, 0.045 g, 0.00011 mol, prepared as described in Example 27) was added methanol (10 mL) and sodium borohydride (0.00428 g, 0.000113 mol). The reaction was allowed to stir at 50° C. overnight. The volatiles were removed from the reaction, and the resulting material was extracted with ethyl acetate and 1M aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with dichloromethane followed by 1% methanol in dichloromethane to give the compound (P-0050, 31 mg, 68%). MS (ESI) [M+H+]+=399.2.

Workup

  1. customThe volatiles were removed from the reaction
  2. extractionthe resulting material was extracted with ethyl acetate and 1M aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with dichloromethane
  8. customto give the compound (P-0050, 31 mg, 68%)

Sources & evidence

ORD record
ord-2a7b8913db06428190c9688f9251f34d
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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