HCID 71284568, compound → HCID 71284885, compound

HRID 1481806Notes

Reaction equation

HRID 1481806 reaction equation
C([O:8][C:9]1[C:14]([C:15]([O:17]CC2C=CC=CC=2)=[O:16])=[C:13]([O:25]CC2C=CC=CC=2)[N:12]=[C:11]([C:33]2[CH:41]=[C:40]3[C:36]([C:37]4[CH2:45][CH2:44][N:43](C(OC(C)(C)C)=O)[CH2:42][C:38]=4[NH:39]3)=[CH:35][CH:34]=2)[C:10]=1[CH2:53][CH3:54])C1C=CC=CC=1>C(O)(C(F)(F)F)=O.[SiH](C(C)C)(C(C)C)C(C)C>[CH2:53]([C:10]1[C:9]([OH:8])=[C:14]([C:15]([OH:17])=[O:16])[C:13](=[O:25])[NH:12][C:11]=1[C:33]1[CH:41]=[C:40]2[C:36]([C:37]3[CH2:45][CH2:44][NH:43][CH2:42][C:38]=3[NH:39]2)=[CH:35][CH:34]=1)[CH3:54]

Participants

4

Reactant 1

HCID 71284568HCID 71284568, compound

Product 1

HCID 71284885HCID 71284885, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 138754Silane, tris(1-methylethyl)-Solvent

Procedure

A mixture of tert-butyl 7-(4,6-bis(benzyloxy)-5-(benzyloxycarbonyl)-3-ethylpyridin-2-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (20 mg, 0.027 mmol) in TFA (0.2 mL) and TIPSH (0.2 mL) was stirred at room temperature for 15 h. The solvents were removed and the residue was stirred in 10% MeOH in CH2Cl2 (0.5 mL). The resulting solid was collected by filtration and washed with CH2Cl2 to give the title compound as an off-white solid (10 mg, TFA salt, 78%).

Workup

  1. customThe solvents were removed
  2. stirringthe residue was stirred in 10% MeOH in CH2Cl2 (0.5 mL)
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-c3fb6625adf1481bb217c14d6d8ffbd9
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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