Hydrochloride methanol → HCID 178508049, compound

HRID 1466643Notes

Reaction equation

HRID 1466643 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH:30]2[CH2:32][CH2:31]2)=[C:6]([C:8]2[C:12]([NH:13]C(=O)OC(C)(C)C)=[CH:11][N:10](COCC[Si](C)(C)C)[N:9]=2)[CH:7]=1.ClC1C=CC(OC2CC2)=C(C2N(COCC[Si](C)(C)C)N=CC=2NC(=O)OC(C)(C)C)C=1.Cl.CO>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH:30]2[CH2:32][CH2:31]2)=[C:6]([C:8]2[C:12]([NH2:13])=[CH:11][NH:10][N:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 21893726Hydrochloride methanolHCID 66852002tert-butyl 5-(5-chloro-2-cyclopropoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-ylcarbamateHCID 70496613Tert-butyl 3-(5-chloro-2-cyclopropoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-ylcarbamate

Product 1

HCID 178508049HCID 178508049, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tert-butyl 3-(5-chloro-2-cyclopropoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-ylcarbamate and tert-butyl 5-(5-chloro-2-cyclopropoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-ylcarbamate were dissolved in 50 mL of MeOH. 50 mL of 4 M HCl/MeOH was added dropwise. The mixture was stirred at room temperature overnight. The mixture was evaporated to dryness and purified by silica gel chromatography, eluting with EtOAc to afford 0.25 g of 3-(5-chloro-2-cyclopropoxyphenyl)-1H-pyrazol-4-amine. LCMS (ESI) m+H=249.8. 1H NMR (DMSO-d6, 400 MHz) δ: 12.32-12.10 (br, 1H), 7.41-7.34 (m, 3H), 7.09 (s, 1H), 4.12 (q, J=5.2 Hz, 2H), 2.94-3.88 (m, 3H), 0.79-0.74 (m, 4H)

Workup

  1. customThe mixture was evaporated to dryness
  2. custompurified by silica gel chromatography
  3. washeluting with EtOAc

Sources & evidence

ORD record
ord-7ac87f60e81041a684e6ce70258f12b0
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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