1,2-Dichloroethane → 5-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid {1-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-1H-pyrazol-3-yl}-amide

HRID 2065003Notes

Reaction equation

HRID 2065003 reaction equation
N#N.[C:3]([Si:7]([CH3:26])([CH3:25])[O:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[O:21][CH:20]=[N:19][C:18]=2[C:22](O)=[O:23])[CH:14]=[CH:15][CH:16]=1)([CH3:6])([CH3:5])[CH3:4].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[CH3:50][C:51]1([C:56]2[O:60][C:59]([CH2:61][N:62]3[CH:66]=[CH:65][C:64]([NH2:67])=[N:63]3)=[CH:58][CH:57]=2)[O:55][CH2:54][CH2:53][O:52]1>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[CH3:50][C:51]1([C:56]2[O:60][C:59]([CH2:61][N:62]3[CH:66]=[CH:65][C:64]([NH:67][C:22]([C:18]4[N:19]=[CH:20][O:21][C:17]=4[C:13]4[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][CH2:9][O:8][Si:7]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:26])[CH3:25])[CH:12]=4)=[O:23])=[N:63]3)=[CH:58][CH:57]=2)[O:55][CH2:54][CH2:53][O:52]1

Participants

10

Reactant 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669287811-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-1H-pyrazol-3-ylamineHCID 669288865-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid

Product 1

HCID 669291035-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid {1-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-1H-pyrazol-3-yl}-amide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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-{3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid (130 mg, 0.37 mmol) in CH2Cl2 (2.7 mL) was treated sequentially with DMAP (11 mg, 0.09 mmol), HOBt (60 mg, 0.45 mmol), EDC (179 mg, 0.94 mmol) and DIPEA (0.25 mL, 1.50 mmol) and the reaction mixture was stirred at rt for 1 h. A solution of 1-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-1H-pyrazol-3-ylamine (93 mg, 0.37 mmol) in CH2Cl2 (1.0 mL) was then added and the reaction mixture was stirred at rt for 48 h. CH2Cl2 (10 mL) was added followed by water (10 mL). The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (1:2 hept-EA) gave the title compound as a colorless oil. TLC: rf (1:2 hept-EA)=0.26. LC-MS-conditions 02: tR=1.22 min, [M+H]+=579.74.

Workup

  1. stirringthe reaction mixture was stirred at rt for 48 h
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customPurification of the residue by FC (1:2 hept-EA)

Sources & evidence

ORD record
ord-f85ae924f7f8497290962564ccba97e7
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

Loading…