Tetrahydrofuran → HCID 66571138, compound

HRID 924681Notes

Reaction equation

HRID 924681 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([OH:23])=O)[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:24][N:25](C=O)C.C1COCC1.C1COCC1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN.O>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([NH:25][CH3:24])=[O:23])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 70979820HCID 70979820, compound

Product 1

HCID 66571138HCID 66571138, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6329MethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1H-pyrrole-3-carboxylic acid (142 mg, 0.43 mmol) in DMF/THF 1/1 (4 mL) DIPEA (0.301 mL, 1.72 mmol) and MeNH2 2 M in THF (0.432 mL, 0.86 mmol) were added and the solution was stirred at 0° C. EDCl (157 mg, 0.86 mmol) and HOBT (117 mg, 0.86 mmol) were added and the reaction mixture was stirred for 4 h at room temperature. The mixture was diluted with water and extracted with DCM (4×10 mL). The organic phase was washed with brine, water and then dried over sodium sulfate and concentrated. The crude material was chromatographed on silica gel (DCM/MeOH 90/10) to afford the title compound (124 mg, 84%).

Workup

  1. stirringthe reaction mixture was stirred for 4 h at room temperature
  2. extractionextracted with DCM (4×10 mL)
  3. washThe organic phase was washed with brine, water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude material was chromatographed on silica gel (DCM/MeOH 90/10)

Sources & evidence

ORD record
ord-ce5a5767d8da4d5dae6a3ca99000057a
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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