Cesium carbonate → tert-butyl(S)-1-(4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)propan-2-ylcarbamate

HRID 521629Notes

Reaction equation

HRID 521629 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)[CH:3]=1.[C:15]([O:19][C:20]([NH:22][C@@H:23]([CH3:30])[CH2:24]OS(C)(=O)=O)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:30][C@@H:23]([NH:22][C:20](=[O:21])[O:19][C:15]([CH3:16])([CH3:18])[CH3:17])[CH3:24])=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 10753379(S)-Methanesulphonic acid 2-Boc-aminopropyl esterHCID 1355820244-amino-2-(1-methyl-1H-pyrazol-5-yl)phenol

Product 1

HCID 86633183tert-butyl(S)-1-(4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)propan-2-ylcarbamateYield 34.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Amino-2-(1-methyl-1H-pyrazol-5-yl)phenol (300.00 mg, 1585.5 μmol), methanesulfonic acid 2-(S)-tert-butoxycarbonylamino-propyl ester (602.45 mg, 2378.3 μmol) and Cesium carbonate (1033.2 mg, 3171.0 μmol) were dissolved in acetone, and heated in the microwave at 130 C for 1 hour. The reaction mixture was filtered and the filtrate removed under vacuum. The residue was dissolved in DCM; washed with 1N NaOH (3×) and then removed under vacuum to yield a brownish residue in 34.6% yield. LCMS m/z=347.3 (M+H); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16 (d, J=6.32 Hz, 3H), 1.38 (s, 9H), 3.65 (s, 3H), 3.67-3.77 (m, 3H), 6.23 (d, J=1.77 Hz, 1H), 6.84 (s, 1H), 6.95 (s, 1H), 7.11 (s, 1H), 7.44 (d, J=1.77 Hz, 1H).

Workup

  1. temperatureheated in the microwave at 130 C for 1 hour
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate removed under vacuum
  4. dissolutionThe residue was dissolved in DCM
  5. washwashed with 1N NaOH (3×)
  6. customremoved under vacuum
  7. customto yield a brownish residue in 34.6% yield

Sources & evidence

ORD record
ord-67114019dd954e84bc54c49a24238c5e
Source dataset
uspto-grants-2016_05
Patent number
US09328107B2

Reaction notes

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