1-Hydroxybenzotriazole → HCID 86616218, compound

HRID 1817846Notes

Reaction equation

HRID 1817846 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[C:33]([N:40]1[CH2:48][CH2:47][CH2:46][C@H:42]([C:43]([OH:45])=O)[CH2:41]1)([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].CCN(C(C)C)C(C)C.[CH3:58][O:59][C:60]1[CH:65]=[CH:64][C:63]([CH2:66][CH2:67][CH3:68])=[CH:62][C:61]=1[C:69]1[N:70]=[C:71]([NH2:74])[S:72][CH:73]=1>CN(C=O)C.CCOC(C)=O>[CH3:58][O:59][C:60]1[CH:65]=[CH:64][C:63]([CH2:66][CH2:67][CH3:68])=[CH:62][C:61]=1[C:69]1[N:70]=[C:71]([NH:74][C:43]([C@H:42]2[CH2:46][CH2:47][CH2:48][N:40]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[CH2:41]2)=[O:45])[S:72][CH:73]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42684674-(2-Methoxy-5-propylphenyl)-2-thiazolamineHCID 6951168(3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 86616218HCID 86616218, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.5 g of TBTU, 0.1 g of HOBT, 0.35 g of (S)-N-Boc-nipecotic acid and then 0.3 mL of DIPEA are added, at a temperature of 0° C., to a solution of 0.5 g of 4-(2-methoxy-5-propylphenyl)-1,3-thiazol-2-amine, obtained in preparation I.4, in 4 mL of DMF. The medium is stirred at room temperature for 3 hours and then diluted with EtOAc and washed 4 times with 10% Na2CO3 solution and then with saturated NaCl solution. After drying over MgSO4, the solution is concentrated and then purified by flash chromatography to give 0.56 g of a white solid.

Workup

  1. washwashed 4 times with 10% Na2CO3 solution
  2. dry with materialAfter drying over MgSO4
  3. concentrationthe solution is concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-91b4f0677a6b43caaa82f2460c96f96f
Source dataset
uspto-grants-2009_10
Patent number
US07598392B2

Reaction notes

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