1,2-Dichloroethane → 5-Phenyl-oxazole-4-carboxylic acid (1-{2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-1H-pyrazol-3-yl)-amide

HRID 2065061Notes

Reaction equation

HRID 2065061 reaction equation
N#N.[C:3]1([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14]([OH:16])=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[C:31]([Si:35]([CH3:52])([CH3:51])[O:36][CH:37]([C:39]1[O:40][C:41]([CH2:44][N:45]2[CH:49]=[CH:48][C:47]([NH2:50])=[N:46]2)=[CH:42][N:43]=1)[CH3:38])([CH3:34])([CH3:33])[CH3:32]>C(Cl)Cl.O>[C:31]([Si:35]([CH3:52])([CH3:51])[O:36][CH:37]([C:39]1[O:40][C:41]([CH2:44][N:45]2[CH:49]=[CH:48][C:47]([NH:50][C:14]([C:10]3[N:11]=[CH:12][O:13][C:9]=3[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:16])=[N:46]2)=[CH:42][N:43]=1)[CH3:38])([CH3:34])([CH3:33])[CH3:32]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 669294421-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-1H-pyrazol-3-ylamine

Product 1

HCID 669290295-Phenyl-oxazole-4-carboxylic acid (1-{2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-1H-pyrazol-3-yl)-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-phenyl-oxazole-4-carboxylic acid (114 mg, 0.60 mmol) in CH2Cl2 (3.0 mL) was treated at rt with HOBt (98 mg, 0.72 mmol), EDC (289 mg, 1.51 mmol) DMAP (18 mg, 0.15 mmol) and the resulting mixture was stirred at rt for 30 min. 1-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-1H-pyrazol-3-ylamine (297 mg, 0.60 mmol) in CH2Cl2 (3.0 mL) was then added and the resulting mixture was stirred at rt for 16 h. CH2Cl2 (20 mL) followed by water (15 mL) were added and the aqueous phase was extracted with CH2Cl2. The combined organic phases were washed with water, brine, dried over MgSO4, filtered, and the solvent removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 02: tR=1.17 min, [M+H]+=494.56.

Workup

  1. stirringthe resulting mixture was stirred at rt for 16 h
  2. additionwere added
  3. extractionthe aqueous phase was extracted with CH2Cl2
  4. washThe combined organic phases were washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d162557d46b044979a29cfcfa3e4861a
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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