Morpholine → HCID 59644534, compound

HRID 2252006Notes

Reaction equation

[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]1[C:11]([Cl:12])=[C:10]([C:13]2[O:17][N:16]=[C:15]([CH2:18][OH:19])[C:14]=2[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2Cl)=[O:21])[N:9]=[N:8]1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>CCOC(C)=O>[F:36][C:2]([F:1])([F:37])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:33])([F:35])[F:34])[CH:31]=1)[CH2:6][N:7]1[C:11]([Cl:12])=[C:10]([C:13]2[O:17][N:16]=[C:15]([CH2:18][OH:19])[C:14]=2[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[O:21])[N:9]=[N:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve {5-[1-(3,5-bis-trifluoromethyl-benzyl)-5-chloro-1H-[1,2,3]triazol-4-yl]-3-hydroxymethyl-isoxazol-4-yl}-(2-chloro-phenyl)-methanone (0.10 g, 018 mmol) in morpholine (1.0 mL) and stir at 80° C. for 20 hours. Dilute the solution with EtOAc (25 mL) and wash with 1N HCl (20 mL), water (20 mL), and saturated NaHCO3 (20 mL) then dry, filter, and concentrate. Purify the crude material by flash chromatography to give the title compound: MS (IS) 615.9 (M+1), MS (ES−) 613.9 (M−1): 1HNMR (400 MHz, CDCl3) δ 7.95 (s, 1H), 7.74 (s, 2H), 7.45 (dd, 1H, J=1.4, 7.5), 6.93 (dt, 1H, J=1.5, 7.4), 6.83 (dt, 1H, J=1.0, 7.4), 6.40 (m, 1H), 5.42 (s, 2H), 4.85 (d, 2H, J=7.3), 3.80 (t, 1H, J=7.3), 3.44 (m, 4H), 2.64 (m, 4H).

Workup

washwash with 1N HCl (20 mL), water (20 mL), and saturated NaHCO3 (20 mL)
customthen dry
filtrationfilter
concentrationconcentrate
customPurify the crude material by flash chromatography

Sources & evidence

ORD record: ord-ea5d04f38941422da08c9ff936e78219
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320994B2

Reaction notes

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