Ammonia → HCID 86725298, compound

HRID 1403230Notes

Reaction equation

HRID 1403230 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[CH3:28])=[C:10]([C:29](O)=[O:30])[CH:9]=2)[C:5]([C:32]#[CH:33])=[CH:4][N:3]=1.CC[N:36](C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.N>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:20])[CH3:19])[C:11]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[CH3:28])=[C:10]([C:29]([NH2:36])=[O:30])[CH:9]=2)[C:5]([C:32]#[CH:33])=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86725297HCID 86725297, compound

Product 1

HCID 86725298HCID 86725298, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(2-amino-5-ethynylpyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylic acid (338 mg, 0.7 mmol) in dry THF (5 mL) and DIPEA (0.48 mL, 2.8 mmol) was stirred at 0° C. EDCl (268 mg, 1.4 mmol), HOBT.NH3 (213 mg, 1.4 mmol) were added and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated, the residue taken-up in saturated solution of NaHCO3 and extracted with EtOAc. The combined organic layers were dried over sodium sulfate to obtain the title compound as a light-orange oil (334 mg, 99%).

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue taken-up in saturated solution of NaHCO3 and extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over sodium sulfate

Sources & evidence

ORD record
ord-9484da74b8f8417eac58d25cc37c6071
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…