1-Hydroxybenzotriazole → HCID 57912296, compound

HRID 389014Notes

Reaction equation

HRID 389014 reaction equation
CN(C(O[N:9]1N=N[C:11]2[CH:12]=CC=C[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[Si:35]([O:42][CH2:43][C:44]1[C:45]([N+:53]([O-:55])=[O:54])=[C:46]([CH:50]=[CH:51][CH:52]=1)[C:47]([OH:49])=O)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].C(N(CC)C(C)C)(C)C.C(N)C#C>CN(C=O)C.CCOC(C)=O>[Si:35]([O:42][CH2:43][C:44]1[C:45]([N+:53]([O-:55])=[O:54])=[C:46]([CH:50]=[CH:51][CH:52]=1)[C:47]([NH:9][CH2:10][C:11]#[CH:12])=[O:49])([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 239041PropargylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57912300HCID 57912300, compound

Product 1

HCID 57912296HCID 57912296, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HBTU (183 mg, 0.482 mmol) and HOBt (65.1 mg, 0.482 mmol) were added to a stirring solution of Compound 10 (150 mg, 0.482 mmol) in anhydrous DMF (4.82 mL) followed by N,N-diisopropylethylamine (187 mg, 1.45 mmol) and propargyl amine (79.6 mg, 1.45 mmol). The resulting solution was stirred for 30 h at room temperature after which time 25 mL of EtOAc were added and the solution was washed with water (3×10 mL), aqueous saturated NH4Cl (1×10 mL), and brine (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated on a rotary evaporator. The resulting oil was purified by silica gel chromatography (50% EtOAc:hexanes) to yield Compound 11 as a white solid (92.3 mg, 55%).

Workup

  1. additionwere added
  2. washthe solution was washed with water (3×10 mL), aqueous saturated NH4Cl (1×10 mL), and brine (1×10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. customThe resulting oil was purified by silica gel chromatography (50% EtOAc:hexanes)

Sources & evidence

ORD record
ord-15f6c3ffc1414dcc87cc1d0c724fac23
Source dataset
uspto-grants-2013_02
Patent number
US08378041B2

Reaction notes

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