HCID 22064189, compound → HCID 10436524, compound

HRID 1827897Notes

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:24])[CH2:14][N:15]3[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])C)[CH2:17][CH2:16]3)=[CH:7][C:5]=2[N:6]=1.ClCC1[O:28][C:29]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:32][C:30]=2[N:31]=1>CN(C=O)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:24])[CH2:14][N:15]3[CH2:16][CH2:17][N:18]([CH2:21][C:23]4[O:28][C:29]5[CH:35]=[CH:34][C:33]([C:36]6[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=6)=[CH:32][C:30]=5[N:31]=4)[CH2:19][CH2:20]3)=[CH:7][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 150 °C

Procedure

(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-(4-prop-2-ylpiperazinyl)propan-2-ol (0.035 g, 0.11 mmol) and DMF (1 mL) were placed in a Smith Process Vial™ (3 mL glass vessel) followed by the addition of 2-(chloromethyl)-5-phenyl-benzoxazole (0.027 g, 0.11 mmol). The vial was sealed and the mixture was heated in the Emrys Optimizer™ microwave at 150° C. for 300 sec, fixed hold time on, absorption level normal, pre-stirring 10 s. It was then cooled to room temperature, evaporated under reduced pressure and the residue was purified by flash chromatography (3% MeOH in CH2Cl2) to yield (2R)-3-(2-methylbenzothiazol-5-yloxy)-1-{4-[(5-phenylbenzoxazol-2-yl)methyl]piperazinyl}propan-2-ol as a off-white solid.

Workup

customThe vial was sealed
customabsorption level normal
temperatureIt was then cooled to room temperature
customevaporated under reduced pressure
customthe residue was purified by flash chromatography (3% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-f2c09dc8d1554dbe864cabf1a67da43d
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056924B2

Reaction notes

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