Triethylamine → HCID 86630150, compound

HRID 908408Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:14]=[N:15][N:16]([CH2:18][CH2:19][OH:20])[CH:17]=2)=[CH:9][C:8]=1[C:21]1[O:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:20][CH2:19][CH2:18][N:16]1[CH:17]=[C:13]([C:10]2[CH:11]=[N:12][C:7]([NH2:6])=[C:8]([C:21]3[O:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[N:25]=3)[CH:9]=2)[CH:14]=[N:15]1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methanesulphonyl chloride (0.072 ml) was added to 2-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]pyrazol-1-yl]ethanol (150 mg, Example 28), triethylamine (0.130 ml) dissolved dichloromethane (5 ml) at 0° C. The resulting suspension was stirred at 0° C. for 2 hours. The mixture was adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 1 to 4% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 2-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]pyrazol-1-yl]ethyl methanesulphonate (150 mg) as a solid. NMR Spectrum: (CDCl3) 3.11 (s, 3H), 4.49 (t, 2H), 4.62 (t, 2H), 7.41-7.49 (m, 2H), 7.68 (bs, 2H), 7.78-7.82 (m, 1H), 7.83-7.87 m, 1H), 8.01 (d, 1H), 8.31 (d, 1H), 8.43 (d, 1H), 8.53 (d, 1H); Mass spectrum: M+H+ 400.

Workup

custompurified by flash chromatography on silica gel eluting with 1 to 4% methanolic ammonia (7 N) in dichloromethane
customThe solvent was evaporated to dryness

Sources & evidence

ORD record: ord-cb713e97f75a488d9c610eb01f394ff4
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

Loading…