Sodium borohydride → HCID 69284744, compound

HRID 75893Notes

Reaction equation

HRID 75893 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:17]([F:18])=[CH:16][C:13]([CH:14]=[O:15])=[C:12]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH3:21])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[N:11]=[C:12]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH3:21])[C:13]([CH2:14][OH:15])=[CH:16][C:17]=3[F:18])[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86620610(S)-6-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)nicotinaldehyde

Product 1

HCID 69284744HCID 69284744, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-(1-(4-fluorophenyl)ethylamino)nicotinaldehyde (Example 73; 0.10 g, 0.26 mmol) in MeOH (5 ml) at 0° C. was added NaBH4 (0.012 g, 0.33 mmol). The reaction was stirred for 10 minutes, and then quenched with water and extracted with DCM (2×20 ml). The combined organic fractions were dried over Na2SO4, filtered, and then concentrated. The resulting oil was purified by column chromatography (DCM-MeOH=100:1) to give the title compound (0.088 g, 88%). 1H NMR (400 MHz, CD3OD) δ 7.42-7.39 (m, 2H), 7.16-7.01 (m, 1H), 7.01 (br s, 2H), 6.06-5.41 (m, 1H), 5.19-5.02 (m, 1H), 4.52 (br s, 2H), 1.88-1.81 (m, 1H), 1.53 (d, J=6.6 Hz, 3H), 0.97-0.91 (m, 2H), 0.65 (br s, 2H). MS: Calcd.: 385. Found: [M+H]+ 386.

Workup

  1. customquenched with water
  2. extractionextracted with DCM (2×20 ml)
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was purified by column chromatography (DCM-MeOH=100:1)

Sources & evidence

ORD record
ord-fd524d49a97641428337359d4146f237
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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