Triethylamine → (2R)-3-(2-methylbenzothiazol-5-yloxy)-1-[4-({5-[4-(trifluoromethyl)phenyl](4,5-dihydroisoxazol-3-yl)}methyl)piperazinyl]propan-2-ol

HRID 1795028Notes

Reaction equation

[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@H:13]([OH:21])[CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.Cl[CH2:30][C:31]1[CH2:35][CH:34]([C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)[O:33][N:32]=1>C(O)(CC)(C)C>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@H:13]([OH:21])[CH2:14][N:15]3[CH2:16][CH2:17][N:18]([CH2:30][C:31]4[CH2:35][CH:34]([C:36]5[CH:41]=[CH:40][C:39]([C:42]([F:44])([F:43])[F:45])=[CH:38][CH:37]=5)[O:33][N:32]=4)[CH2:19][CH2:20]3)=[CH:7][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a stirred mixture of (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol (30 mg, 0.08 mmol) in tert-amylalcohol (5 mL) was added triethylamine (40 μL, 0.30 mmol), followed by 3-(chloromethyl)-5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole (20 mg, 0.08 mmol). The resulting mixture was stirred at 95° C. for 12 hours, concentrated under reduced pressure, and purified by preparative chromatograph (1:19 MeOH:CH2Cl2) to afford (2R)-3-(2-methylbenzothiazol-5-yloxy)-1-[4-({5-[4-(trifluoromethyl)phenyl](4,5-dihydroisoxazol-3-yl)}methyl)piperazinyl]propan-2-ol (10 mg, M+1=535.1).

Workup

concentrationconcentrated under reduced pressure
custompurified by preparative chromatograph (1:19 MeOH:CH2Cl2)

Sources & evidence

ORD record: ord-e2cf7a390fc24da4b4f13c7113c4280b
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026321B2

Reaction notes

Loading…