Sodium borohydride → HCID 59216527, compound

HRID 2069801Notes

Reaction equation

HRID 2069801 reaction equation
[F:1][CH:2]([F:48])[C:3]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[N:11]([C:17]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[CH:30]=[C:29]([NH:31][C:32]5[CH:37]=[CH:36][C:35]([C:38]([N:40]6[CH2:45][CH2:44][O:43][CH2:42][CH2:41]6)=[O:39])=[CH:34][N:33]=5)[C:28](=[O:46])[N:27]([CH3:47])[CH:26]=4)[C:18]=2[CH:19]=[O:20])[CH2:10][CH2:9]3)[CH2:5][CH2:4]1.[BH4-].[Na+]>C1COCC1>[F:48][CH:2]([F:1])[C:3]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[N:11]([C:17]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[CH:30]=[C:29]([NH:31][C:32]5[CH:37]=[CH:36][C:35]([C:38]([N:40]6[CH2:41][CH2:42][O:43][CH2:44][CH2:45]6)=[O:39])=[CH:34][N:33]=5)[C:28](=[O:46])[N:27]([CH3:47])[CH:26]=4)[C:18]=2[CH2:19][OH:20])[CH2:10][CH2:9]3)[CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59216437HCID 59216437, compound

Product 1

HCID 59216527HCID 59216527, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[6-(1-Difluoromethyl-cyclopropyl)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde (0.025 g, 0.038 mmole) was dissolved into THF (2 ml). To this solution was added NaBH4 (0.006 g, 0.015 mmole) and the mixture stirred at room temperature 0.5 hour after which it was quenched with ice water (4 ml) and extracted with ethylacetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC to afford 6-(1-Difluoromethyl-cyclopropyl)-2-(2-hydroxymethyl-3-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-3,4-dihydro-2H-isoquinolin-1-one (XI), 0.020 g (80% yield).

Workup

  1. customwas quenched with ice water (4 ml)
  2. extractionextracted with ethylacetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-34f9f87da6f146ec8757103691ecf244
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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