Dichloromethane → HCID 46866598, compound

HRID 2069857Notes

Reaction equation

HRID 2069857 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]([N:40]5[CH2:45][CH2:44][O:43][CH2:42][CH2:41]5)=[O:39])=[CH:34][N:33]=4)[C:28](=[O:46])[N:27]([CH3:47])[CH:26]=3)[C:18]=1[CH:19]=[O:20])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]([N:40]5[CH2:45][CH2:44][O:43][CH2:42][CH2:41]5)=[O:39])=[CH:34][N:33]=4)[C:28](=[O:46])[N:27]([CH3:47])[CH:26]=3)[C:18]=1[CH2:19][OH:20])[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 594738092-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde

Product 1

HCID 46866598HCID 46866598, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

69 mg of 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde was weighed into a 20 mL reaction vial fitted with a stir bar and cap. Added 2 mL of CH2Cl2 and 2 mL MeOH and stirred to obtain a clear amber solution. Added 14 mg of sodium borohydride. Stirred at room temperature for 3 hr. Quenched with 5 mL of saturated aqueous NH4Cl. Separated phases and extracted the aqueous phase with 2×2 mL CH2Cl2. Washed the combined organic phases with 5 mL of saturated aqueous NaHCO3. Dried over Na2SO4 and removed the solvent on rotavap. Crystallized the residue from isopropyl acetate to obtain 52 mg of the title compound as a white solid. MS (ESI) 639 (M+H)+.

Workup

  1. customvial fitted with a stir bar
  2. customcap
  3. customto obtain a clear amber solution
  4. stirringStirred at room temperature for 3 hr
  5. customQuenched with 5 mL of saturated aqueous NH4Cl
  6. extractionSeparated phases and extracted the aqueous phase with 2×2 mL CH2Cl2
  7. washWashed the combined organic phases with 5 mL of saturated aqueous NaHCO3
  8. dry with materialDried over Na2SO4
  9. customremoved the solvent on rotavap
  10. customCrystallized the residue from isopropyl acetate

Sources & evidence

ORD record
ord-f8c9c03373094c8a82041b0afad19266
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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