Nitrogen → {1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-1H-pyrazol-4-yl}-carbamic acid 2-chloro-benzyl ester

HRID 2065088Notes

Reaction equation

HRID 2065088 reaction equation
N#N.[C:3]([SiH2:7][O:8][C:9]([CH3:23])([CH3:22])[C:10]1[O:11][CH:12]=[C:13]([CH2:15][N:16]2[CH:20]=[C:19]([NH2:21])[CH:18]=[N:17]2)[N:14]=1)([CH3:6])([CH3:5])[CH3:4].CCN(C(C)C)C(C)C.[CH:33]1[CH:38]=[C:37]([CH2:39][O:40][C:41](Cl)=[O:42])[C:36]([Cl:44])=[CH:35][CH:34]=1>C(Cl)Cl.O>[Cl:44][C:36]1[CH:35]=[CH:34][CH:33]=[CH:38][C:37]=1[CH2:39][O:40][C:41](=[O:42])[NH:21][C:19]1[CH:18]=[N:17][N:16]([CH2:15][C:13]2[N:14]=[C:10]([C:9]([CH3:23])([CH3:22])[O:8][SiH2:7][C:3]([CH3:6])([CH3:4])[CH3:5])[O:11][CH:12]=2)[CH:20]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 40723422-Chlorobenzyl chloroformateHCID 1317300151-[2-(tert-Butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-1H-pyrazol-4-ylamine

Product 1

HCID 131730016{1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-1H-pyrazol-4-yl}-carbamic acid 2-chloro-benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-1H-pyrazol-4-ylamine (347 mg, 1.12 mmol) in CH2Cl2 (5.0 mL) was treated with DIPEA (0.31 mL, 1.78 mmol) followed by 2-chlorobenzylchloroformate (0.23 mL, 1.45 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and water (5.0 mL) was added. The layers were separated and the aq. layer extracted with CH2Cl2 (2×10 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (9:1 to 1:1 hept-EA) gave the title compound as an orange oil. TLC: rf (1:1 hept-EA)=0.27. LC-MS-conditions 02: tR=1.13 min; [M+H]+=476.95.

Workup

  1. customThe layers were separated
  2. extractionthe aq. layer extracted with CH2Cl2 (2×10 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (9:1 to 1:1 hept-EA)

Sources & evidence

ORD record
ord-46a1be41bf554b0491d4ef0ca80ba05a
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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