HCID 67054988, compound → HCID 67054961, compound

HRID 1772785Notes

Reaction equation

HRID 1772785 reaction equation
[F:1][CH2:2][CH:3]([N:21]1[CH:25]=[C:24]([C:26]2[C:27]3[CH:34]=[CH:33][N:32]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:28]=3[N:29]=[CH:30][N:31]=2)[CH:23]=[N:22]1)[CH2:4][N:5]1[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7][CH2:6]1.FCC(N1CCN(C(OCC2C=CC=CC=2)=O)CC1)CN1C=C(C2C3C=CN(COCC[Si](C)(C)C)C=3N=CN=2)C=N1.[H][H]>CO.[Pd]>[F:1][CH2:2][CH:3]([N:21]1[CH:25]=[C:24]([C:26]2[C:27]3[CH:34]=[CH:33][N:32]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:28]=3[N:29]=[CH:30][N:31]=2)[CH:23]=[N:22]1)[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 67054988HCID 67054988, compoundHCID 67054994HCID 67054994, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67054961HCID 67054961, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (±)-benzyl 4-{3-fluoro-2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}piperazine-1-carboxylate (0.064 g, 0.11 mmol) and (±)-benzyl 4-(2-fluoro-1-{[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]methyl}ethyl)piperazine-1-carboxylate (0.064 g, 0.11 mmol) in 5 mL of methanol was hydrogenated in the presence of 5% Pd/C, under balloon pressure of hydrogen, for 2 h. After filtering off the catalyst, the filtrate was concentrated and used directly in next step. LCMS calculated for C22H35FN7OSi(M+H)+: m/z=460.3; Found: 460.4.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4e5e3db1384b460aa080a95cc8e72164
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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