Water → HCID 71143669, compound

HRID 627794Notes

Reaction equation

HRID 627794 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[C:21]([N:22]4[CH2:30][C:29]5[C:24](=[CH:25][CH:26]=[C:27]([C:31]#[N:32])[CH:28]=5)[C:23]4=[O:33])=[CH:20][N:19]([C:34]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:16]3=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[BH4-].[Na+].O>C(Cl)Cl.CO>[NH2:32][CH2:31][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:33])[N:22]([C:21]1[C:15]3[C:16](=[N:17][CH:18]=[C:13]([C:10]4[CH:9]=[CH:8][C:7]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[CH:12][CH:11]=4)[N:14]=3)[N:19]([C:34]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:20]=1)[CH2:30]2

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 71143555HCID 71143555, compound

Product 1

HCID 71143669HCID 71143669, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]-1-oxo-isoindoline-5-carbonitrile (111 mg, 0.1586 mmol) dissolved in a mixture of DCM (10 mL) and MeOH (5 mL) under N2. CoCl2 (41.18 mg, 0.3172 mmol) added and resulting green solution cooled in an ice bath. NaBH4 (60 mg, 1.586 mmol) added in one portion and the ice bath removed. After 2 h reaction re-cooled in an ice bath and water (˜5 mL) added. Mixture diluted with DCM (˜20 mL) and stirred vigorously for 20 mins. Layers separated and aqueous extracted with DCM. Aqueous phase basified by addition of sat NaHCO3 solution and extracted with DCM (×2). Combined organics dried and concentrated to give the title compound as a yellow solid 88% pure by UV (112 mg, 82%); MS (ES+) 704.0.

Workup

  1. customresulting green solution
  2. temperaturecooled in an ice bath
  3. customthe ice bath removed
  4. customAfter 2 h reaction
  5. temperaturere-cooled in an ice bath
  6. customLayers separated
  7. extractionaqueous extracted with DCM
  8. additionAqueous phase basified by addition of sat NaHCO3 solution
  9. extractionextracted with DCM (×2)
  10. customCombined organics dried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2338e061897649e091aa11e7ea86d9ae
Source dataset
uspto-grants-2016_04
Patent number
US09309250B2

Reaction notes

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