Ammonia → HCID 86725302, compound

HRID 1403238Notes

Reaction equation

HRID 1403238 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[CH2:20][CH3:21])=[C:10]([C:22]([OH:24])=O)[CH:9]=2)[C:5]([Br:25])=[CH:4][N:3]=1.CC[N:28](C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.N.C(=O)([O-])O.[Na+]>CN(C=O)C>[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[CH2:20][CH3:21])=[C:10]([C:22]([NH2:28])=[O:24])[CH:9]=2)[C:5]([Br:25])=[CH:4][N:3]=1

Participants

8

Reactant 6

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71239580HCID 71239580, compound

Product 1

HCID 86725302HCID 86725302, compoundYield 169.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 5-(2-amino-5-bromopyrimidin-4-yl)-2-(5-chloro-2-ethylphenyl)-1H-pyrrole-3-carboxylic acid (200 mg, 0.47 mmol) in DMF (2 mL) and DIPEA (0.332 mL, 1.89 mmol) was stirred at 0° C. EDCl (180 mg, 0.94 mmol) and HOBT.NH3 (143 mg, 0.94 mmol) were added and the reaction mixture was stirred for 2 h at room temperature. The reaction mixture was poured into saturated solution of sodium hydrogen carbonate. The solid was filtered with suction and the panel washed thoroughly with water and dried under vacuum in an oven at 50° C. The crude compound may be purified by flash chromatography (DCM/MeOH 95/5) to give the title compound (336 mg, 85%).

Workup

  1. filtrationThe solid was filtered with suction
  2. washthe panel washed thoroughly with water
  3. customdried under vacuum in an oven at 50° C
  4. customThe crude compound may be purified by flash chromatography (DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-7af167407518421cbf9f4930792efe18
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…