Ammonium Chloride → N-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-fluoro-1-(3-hydroxybutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246777

Reaction equation

HRID 246777 reaction equation
[Si:1]([O:8][CH2:9][C:10]([NH:13][C:14]([C:16]1[C:20]2=[N:21][C:22]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([F:34])=[CH:31][CH:32]=4)[N:27]([CH2:35][CH2:36][C:37](=[O:39])[CH3:38])[N:26]=3)=[CH:23][N:24]=[C:19]2[N:18]([C:40]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:17]=1)=[O:15])([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].[NH4+].[Cl-]>CO>[Si:1]([O:8][CH2:9][C:10]([NH:13][C:14]([C:16]1[C:20]2=[N:21][C:22]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([F:34])=[CH:31][CH:32]=4)[N:27]([CH2:35][CH2:36][CH:37]([OH:39])[CH3:38])[N:26]=3)=[CH:23][N:24]=[C:19]2[N:18]([C:40]([C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:17]=1)=[O:15])([CH3:11])[CH3:12])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 71279418N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-fluoro-1-(3-oxobutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Product 1

HCID 71279489N-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-fluoro-1-(3-hydroxybutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-fluoro-1-(3-oxobutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (40 mg, 0.05 mmol) in MeOH (5 mL) was added NaBH4 (10 mg, 0.25 mmol) at 0° C. The mixture was stirred at room temperature for 1 hour. NH4Cl (aqueous) was added to the mixture to quench the reaction. The mixture was extracted with EtOAc (3×5 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude was used into the next step without purification. LCMS: (M+H)+=797.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with EtOAc (3×5 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude was used into the next step without purification

Sources & evidence

ORD record
ord-7ee04c01e116446b9e6302262a959d9b
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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