Sodium Iodide → HCID 59557954, compound

HRID 221868Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.Cl[CH2:19][CH2:20][CH2:21][OH:22].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)CCC.CCOC(C)=O.O>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[O:13][CH2:19][CH2:20][CH2:21][OH:22])[N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-(5-amino-3-tert-butyl-pyrazol-1-yl)-phenol (400 mg, 1.73 mmol), 3-chloropropanol (326 mg, 3.46 mmol), potassium carbonate (596 mg, 4.32 mmol) and sodium iodide (77 mg, 0.52 mmol) were combined in n-butanol (6 mL). The reaction mixture was heated at 60° C. for 4 days. The mixture was cooled to room temperature, water (100 mL) and EtOAc (100 mL) were added, and then the organic phase was washed with water and brine, dried (Na2SO4), and concentrated at reduced pressure. The residue was purified by MPLC (80:20 hexane/EtOAc) to give the product 3-[3-(5-amino-3-tert-butyl-pyrazol-1-yl)-phenoxy]-propan-1-ol (400 mg, 80%). 1H-NMR (DMSO-d6) δ 7.30 (t, 1H), 7.10 (m, 2H), 6.80 (d, 1H), 5.30 (s, 1H), 5.10 (bs, 2H), 4.0 (t, 2H), 3.60 (t, 3H), 1.80 (m, 2H), 1.30 (s, 9H); MS LC-MS [M+H]+=290.3, RT=1.05 min.

Workup

temperatureThe mixture was cooled to room temperature
washthe organic phase was washed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated at reduced pressure
customThe residue was purified by MPLC (80:20 hexane/EtOAc)

Sources & evidence

ORD record: ord-c53bd4d3279f46c1b860f83e47a0dc98
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207166B2

Reaction notes

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