Ammonia → HCID 71240190, compound

HRID 1403221Notes

Reaction equation

HRID 1403221 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](O)=[O:22])[CH:9]=2)[C:5]([I:24])=[CH:4][N:3]=1.CC[N:27](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[CH3:20])=[C:10]([C:21]([NH2:27])=[O:22])[CH:9]=2)[C:5]([I:24])=[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 71240245HCID 71240245, compound

Product 1

HCID 71240190HCID 71240190, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 5-(2-amino-5-iodo-pyrimidin-4-yl)-2-(5-chloro-2-methyl-phenyl)-1H-pyrrole-3-carboxylic acid (691 mg, 1.52 mmol) in DMF (5 mL) and DIPEA (1.06 mL, 6.08 mmol) was stirred at 0° C. EDCl (582 mg, 3.04 mmol) and HOBT.NH3 (469 mg, 3.04 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 (518 mg, 75%).

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-83cfe06a918643f8b77fd301b74c16e3
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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