HCID 86681005, compound → HCID 86681006, compound

HRID 1847968Notes

Reaction equation

HRID 1847968 reaction equation
[OH:1][CH2:2][C:3]1[CH:19]=[CH:18][C:6]2[N:7]=[C:8]([NH:10][C@@H:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]3[OH:17])[S:9][C:5]=2[CH:4]=1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[OH:17][C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[NH:10][C:8]1[S:9][C:5]2[CH:4]=[C:3]([CH:2]=[O:1])[CH:19]=[CH:18][C:6]=2[N:7]=1

Participants

4

Reactant 1

HCID 86681005HCID 86681005, compound

Product 1

HCID 86681006HCID 86681006, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,2R)-2-((6-(hydroxymethyl)benzo[d]thiazol-2-yl)amino)cyclohexanol from Step 1 of this Example (445 mg, 1.6 mmol) in CH2Cl2 (40 mL) was added manganese(IV) oxide (696 mg, 8.0 mmol) at rt. The reaction suspension was heated under reflux overnight. After cooling to rt, the reaction mixture was filtered through a Celite pad. The filtrate was concentrated under reduced pressure to give crude 2-(((1R,2R)-2-hydroxycyclohexyl)amino)benzo[d]thiazole-6-carbaldehyde as a brown oil (440 mg, 99%), which was used to next step without further purification. LCMS (ESI) m/z 277 (M+H)+.

Workup

  1. customat rt
  2. temperatureThe reaction suspension was heated
  3. temperatureunder reflux overnight
  4. filtrationthe reaction mixture was filtered through a Celite pad
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7866b07194bb4a8c9aae2c244d609b6a
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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