HCID 67994827, compound → HCID 86681520, compound

HRID 2361315Notes

Reaction equation

HRID 2361315 reaction equation
[Si:1]([O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]4[C:26]([C:27]5[C:28]([CH3:44])=[C:29]([NH:33]C(=O)OCC6C=CC=CC=6)[CH:30]=[CH:31][CH:32]=5)=[CH:25][N:24]=[C:23]([C:45](=[O:47])[NH2:46])[C:19]=4[NH:20]3)=[CH:16][CH:15]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.O1CCCC1.[Pd]>[NH2:33][C:29]1[C:28]([CH3:44])=[C:27]([C:26]2[C:18]3[C:17]4[C:21](=[CH:22][C:14]([N:11]5[CH2:12][CH2:13][CH:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3])[CH2:10]5)=[CH:15][CH:16]=4)[NH:20][C:19]=3[C:23]([C:45]([NH2:46])=[O:47])=[N:24][CH:25]=2)[CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 1

HCID 67994827HCID 67994827, compound

Product 1

HCID 86681520HCID 86681520, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 3-(7-(3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate (0.1164 g, 0.179 mmol) and 10% Pd/C (0.019 g, 0.018 mmol) in methanol (6.7 mL) and tetrahydrofuran (2.2 mL) under hydrogen was stirred for 45 min. After purging with nitrogen, the reaction was filtered through a pad of CELITE® and rinsed with MeOH. The filtrate was concentrated in vacuo, dissolved in CH2Cl2 (75 mL) and washed with brine (25 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to give the desired product (0.0782 g, 0.152 mmol, 85% yield) as a brick-red solid.

Workup

  1. customAfter purging with nitrogen
  2. filtrationthe reaction was filtered through a pad of CELITE®
  3. washrinsed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutiondissolved in CH2Cl2 (75 mL)
  6. washwashed with brine (25 mL)
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7359a90764f457a8c2df8367993cc68
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…