Diisopropylethylamine → HCID 86681005, compound

HRID 1847967Notes

Reaction equation

HRID 1847967 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.CCN(C(C)C)C(C)C.[NH2:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]1[OH:29]>CC(N(C)C)=O>[OH:12][CH2:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:22][C@@H:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]3[OH:29])[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 735777(1R,2R)-2-AminocyclohexanolHCID 57527160HCID 57527160, compound

Product 1

HCID 86681005HCID 86681005, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of (2-bromobenzo[d]thiazol-6-yl)methanol (400 mg, 1.6 mmol) from Step 2 of Example 2 in DMA (6 mL) were added DIEA (258 mg, 2.0 mmol) and (1R,2R)-2-aminocyclohexanol (226 mg, 2.0 mmol) at rt. The reaction mixture was stirred in a sealed tube at 120° C. overnight. After cooling to rt, the mixture was concentrated under reduced pressure to give crude (1R,2R)-2-((6-(hydroxymethyl)benzo[d]thiazol-2-yl)amino)cyclohexanol as a brown oil (445 mg, 100%), which was used for the next step without any further purification. LCMS (ESI) m/z 279 (M+H)+.

Workup

  1. temperatureAfter cooling to rt
  2. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ef0dacbc76cc4c20a6273e69e0db3af2
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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