Dichloromethane → HCID 11725239, compound

HRID 1827458Notes

Reaction equation

HRID 1827458 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21](=[O:26])[NH:22][CH2:23][C:24]#[CH:25])=[CH:11][CH:12]=2)[N:7](C2CCCCO2)[N:6]=1)=[O:4].C(Cl)Cl.OC(C(F)(F)F)=O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21](=[O:26])[NH:22][CH2:23][C:24]#[CH:25])=[CH:11][CH:12]=2)[NH:7][N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 12052TriethylsilaneHCID 21663959HCID 21663959, compoundHCID 23577872HCID 23577872, compound

Product 1

HCID 11725239HCID 11725239, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolved 6-(2-Prop-2-ynylcarbamoyl-phenylamino)-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboxylic acid methylamide (30 mg) in 1.5 mL of a 90:10:1 mixture of CH2Cl2:Trifluoroacetate TFA:triethyl silane and heat to reflux for 2 hours. Diluted the solution with toluene (40 mL) and concentrate by rotary evaporation to an oil. Dissolved the oil in DMF (1 mL), and filter using a 0.2-micron syringe filter. Used prep-HPLC to isolate the desired compound (12 mg, 50%). 1H NMR (CDCl3-d) δ 9.96 (1H, s), 9.49 (1H, s), 8.28 (1H, d, J=8.85 Hz), 7.47 (1H, m), 7.34 (1H, m), 7.22 (1H, m), 7.15 (1H, dd, J1=8.76 Hz, J2=1.79 Hz), 6.99 (1H, m), 6.86 (1H, t, J=6.97 Hz), 6.31 (1H, m), 4.23 (2H, dd, J1=5.18 Hz, J2=2.54 Hz), 3.49 (3H, s), 2.29 (s,1H).

Workup

  1. temperatureto reflux for 2 hours
  2. concentrationconcentrate by rotary evaporation to an oil
  3. dissolutionDissolved the oil in DMF (1 mL)
  4. filtrationfilter
  5. filtrationfilter

Sources & evidence

ORD record
ord-fdcc7702635449d488330f0e7dae7af9
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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