Potassium Carbonate → HCID 57687026, compound

HRID 908403Notes

Reaction equation

Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[C:20]1[C:21]([NH2:31])=[N:22][CH:23]=[C:24]([C:26]2[CH:27]=[N:28][NH:29][CH:30]=2)[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[C:20]1[C:21]([NH2:31])=[N:22][CH:23]=[C:24]([C:26]2[CH:30]=[N:29][N:28]([CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)[CH:27]=2)[CH:25]=1

Participants

Conditions

Temperature: 120 °C

Procedure

4-(2-Chloroethyl)morpholine hydrochloride (101 mg) was added to a stirred solution 3-(1,3-benzoxazol-2-yl)-5-(1H-pyrazol-4-yl)pyridin-2-amine (150 mg, 0.54 mol) and potassium carbonate (164 mg, 1.19 mol) dissolved in DMA (1 ml) over a period of 5 minutes. The resulting solution was stirred at 120° C. for 7 hours. The mixture was filtered. The reaction mixture was purified by preparative HPLC using a Waters X-Terra reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml/minute) and decreasingly polar mixtures of water (containing 1% acetic acid) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford 3-(1,3-benzoxazol-2-yl)-5-[1-(2-morpholinoethyl)pyrazol-4-yl]pyridin-2-amine (134 mg. NMR Spectrum: (CDCl3) 2.27-2.58 (m, 4H), 2.88 (t, 2H), 3.68-3.77 (m, 4H), 4.30 (t, 2H), 6.90 (bs, 2H), 7.34-7.41 (m, 2H), 7.58-7.63 (m, 1H), 7.73 (s, 1H), 7.74-7.77 (m, 1H), 7.79 (s, 1H), 8.38 (d, 1H), 8.39 (d, 1H); Mass spectrum: M+H+ 391.

Workup

filtrationThe mixture was filtered
customThe reaction mixture was purified by preparative HPLC
additionThe fractions containing the desired compound
customwere evaporated to dryness

Sources & evidence

ORD record: ord-7e97728265264c2cb1d86f44d9a593d9
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

Loading…