Water → (1R,2R)-2-((6-((4-bromo-1H-imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol

HRID 1847995Notes

Reaction equation

[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]2[CH:19]=[CH:18][C:11]3[N:12]=[C:13](S(C)=O)[S:14][C:10]=3[CH:9]=2)[CH:6]=1.[NH2:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[OH:27].CCN(C(C)C)C(C)C.O>CC(N(C)C)=O>[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]2[CH:19]=[CH:18][C:11]3[N:12]=[C:13]([NH:20][C@@H:21]4[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]4[OH:27])[S:14][C:10]=3[CH:9]=2)[CH:6]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a suspension of 6-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole (130 mg, 0.37 mmol) from Step 6 of this Example and (1R,2R)-2-aminocyclohexanol (126 mg, 1 mmol) in anhydrous DMA (1.0 mL) was added DIEA (320 μL, 1.8 mmol). The mixture was heated in a sealed tube at 110° C. for 7 h. The mixture was cooled to rt and water was slowly added while stirring to give a precipitate. The mixture stirred for 10 min and the solid was collected by filtration to afford (1R,2R)-2-((6-((4-bromo-1H-imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol (100 mg, 68%) as a tan solid. The material was used in the next step without further purification. LCMS (ESI) m/z 407 and 409 (M+H)+.

Workup

temperatureThe mixture was cooled to rt
customto give a precipitate
stirringThe mixture stirred for 10 min
filtrationthe solid was collected by filtration

Sources & evidence

ORD record: ord-ed34f9c07b0343b2b13ef7084d158a66
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952058B2

Reaction notes

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