HCID 68959969, compound → HCID 178430827, compound

HRID 1892129Notes

Reaction equation

HRID 1892129 reaction equation
[CH:1]([C@@H:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]2[C:11]3[C:18]([CH3:19])=[CH:17][NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:5]1)([CH3:3])[CH3:2].[Br:20][C:21]1[CH:22]=[C:23]([NH:27][C:28](=[N:36][C:37]#[N:38])OC2C=CC=CC=2)[CH:24]=[CH:25][CH:26]=1>C(O)(C)C>[Br:20][C:21]1[CH:22]=[C:23]([NH:27][C:28]([N:9]2[CH2:8][CH2:7][N:6]([C:10]3[C:11]4[C:18]([CH3:19])=[CH:17][NH:16][C:12]=4[N:13]=[CH:14][N:15]=3)[CH2:5][C@@H:4]2[CH:1]([CH3:3])[CH3:2])=[N:36][C:37]#[N:38])[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 68959969HCID 68959969, compoundHCID 178512244HCID 178512244, compound

Product 1

HCID 178430827HCID 178430827, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

The piperazine from step A was combined with phenyl N-3-bromophenyl-N′-cyanocarbamimidate, from example 5, step A, (40 mg, 1.2 mmol) in isopropanol in a sealed tube. The reaction was heated to 120° C., monitored by LC/MS until no starting material remained, and then concentrated under vacuum. The residue was purified by prep HPLC (Sunfire C18 5u 30×100 mm, 10% to 100% B, gradient time=13 min, flow rate=45 ml/min, wavelength=220 nm, solvent A=10 mM aq. Ammonium acetate, solvent B=acetonitrile) to give (S)—N-(3-bromophenyl)-N′-cyano-2-isopropyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboximidamide (2.2 mg, 7%) as a white solid.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by prep HPLC (Sunfire C18 5u 30×100 mm, 10% to 100% B, gradient time=13 min, flow rate=45 ml/min, wavelength=220 nm, solvent A=10 mM aq. Ammonium acetate, solvent B=acetonitrile)

Sources & evidence

ORD record
ord-195dc659852147c882655cde195da2c0
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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