Diisopropylethylamine → HCID 86681242, compound

HRID 1848268Notes

Reaction equation

HRID 1848268 reaction equation
[I:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH2:9][C:10]3[CH:21]=[CH:20][C:13]4[N:14]=[C:15](S(C)=O)[S:16][C:12]=4[CH:11]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.Cl.[NH2:25][C@@H:26]1[CH2:31][CH2:30][CH2:29][C@@H:28]([OH:32])[C@H:27]1[OH:33].CCN(C(C)C)C(C)C>CC(N(C)C)=O>[I:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH2:9][C:10]3[CH:21]=[CH:20][C:13]4[N:14]=[C:15]([NH:25][C@@H:26]5[CH2:31][CH2:30][CH2:29][C@@H:28]([OH:32])[C@H:27]5[OH:33])[S:16][C:12]=4[CH:11]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 701504101161437-13-3HCID 86681243HCID 86681243, compound

Product 1

HCID 86681242HCID 86681242, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 6-((5-iodo-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole (350 mg, 0.8 mmol) and (1R,2S,3R)-3-aminocyclohexane-1,2-diol hydrochloride (258 mg, 1.6 mmol), prepared as described in Gauthier Errasti, et al, Org. Lett. 2009, 13, 2912-2915, in anhydrous DMA (1.5 mL) was added DIEA (402 μL, 2.4 mmol). The mixture was heated in a sealed tube at 120° C. for 15 h. The mixture was cooled to rt and partitioned between EtOAc (150 mL) and 0.5 M aq K2CO3 (100 mL). The organic layer was separated and washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 5% MeOH in DCM to afford (1R,2S,3R)-3-((6-((5-iodo-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexane-1,2-diol (127 mg, 32%) as a yellow solid. LCMS (ESI) m/z 521 (M+H)+.

Workup

  1. customprepared
  2. temperatureThe mixture was cooled to rt
  3. custompartitioned between EtOAc (150 mL) and 0.5 M aq K2CO3 (100 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel flash chromatography
  10. washeluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-11b2fec52f564d1c945a518fa3cdc18b
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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