Sodium Bicarbonate → HCID 58914551, compound

HRID 1297323Notes

Reaction equation

HRID 1297323 reaction equation
[NH2:1][C:2]1[C:3]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[N:4][C:5](Br)=[CH:6][N:7]=1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1B(O)O.C([O-])(O)=O.[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[C:3]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[N:4][C:5]([C:19]2[S:18][CH:22]=[CH:21][CH:20]=2)=[CH:6][N:7]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 248204284-{[(3-Amino-6-bromopyrazin-2-yl)amino]methyl}phenol

Product 1

HCID 58914551HCID 58914551, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-[(3-amino-6-bromo-pyrazin-2-ylamino)-methyl]-phenol (25 mg, 0.085 mmol), 2-thiopheneboronic acid (13 mg, 0.10 mmol), Pd(PPh3)2Cl2 (2 mg, 0.0028 mmol), and NaHCO3 (21 mg, 0.25 mmol) in DME (0.5 mL) and water (0.15 mL) was put in a microwave reaction tube and reacted in a microwave reactor at 110° C. for 7 minutes. The reaction mixture was partitioned in ethyl acetate and water, and the organic layer was evaporated. The residue was purified on a C-18 reversed phase preparative HPLC eluting with Methanol/Acetonitrile containing 0.1% trifluoroacetic acid to 4-[(3-amino-6-thiophen-2-yl-pyrazin-2-ylamino)-methyl]-phenol trifluoroacetic add salt as a white solid (12 mg).

Workup

  1. customwas put in a microwave reaction tube
  2. customreacted in a microwave reactor at 110° C. for 7 minutes
  3. customThe reaction mixture was partitioned in ethyl acetate
  4. customwater, and the organic layer was evaporated
  5. customThe residue was purified on a C-18
  6. washeluting with Methanol/Acetonitrile containing 0.1% trifluoroacetic acid to 4-[(3-amino-6-thiophen-2-yl-pyrazin-2-ylamino)-methyl]-phenol trifluoroacetic add salt as a white solid (12 mg)

Sources & evidence

ORD record
ord-320f613aaf244f46af321a22df8b35e5
Source dataset
uspto-grants-2007_07
Patent number
US07250417B2

Reaction notes

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