Nitrogen → 5-Phenyl-oxazole-4-carboxylic acid [2-(5-acetyl-furan-2-ylmethyl)-thiazol-4-yl]-amide

HRID 1189442Notes

Reaction equation

HRID 1189442 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.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.Cl.[NH2:49][C:50]1[N:51]=[C:52]([CH2:55][C:56]2[O:60][C:59]([C:61](=[O:63])[CH3:62])=[CH:58][CH:57]=2)[S:53][CH:54]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:61]([C:59]1[O:60][C:56]([CH2:55][C:52]2[S:53][CH:54]=[C:50]([NH:49][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:51]=2)=[CH:57][CH:58]=1)(=[O:63])[CH3:62]

Participants

9

Reactant 6

HCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 671287161-[5-(4-Amino-thiazol-2-ylmethyl)-furan-2-yl]-ethanone hydrochloride

Product 1

HCID 671284655-Phenyl-oxazole-4-carboxylic acid [2-(5-acetyl-furan-2-ylmethyl)-thiazol-4-yl]-amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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-1,3-oxazole-4-carboxylic acid (41 mg, 0.21 mmol) in CH2Cl2 (2.0 mL) was treated sequentially with DMAP (6 mg, 0.05 mmol), HOBt (30 mg, 0.22 mmol), EDC.HCl (89 mg, 0.46 mmol) and DIPEA (0.13 mL, 0.74 mmol) and the resulting mixture was stirred at rt for 15 min. This solution was then added to a solution of 1-[5-(4-amino-thiazol-2-ylmethyl)-furan-2-yl]-ethanone hydrochloride (41 mg, 0.19 mmol) in dry CH2Cl2 (0.5 mL) and the reaction mixture was stirred for 16 h at rt. CH2Cl2 (20 mL) was then added and the org. phase was washed with water (15 mL) and brine (15 mL). The org. phase was then dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (1:1 hept:EA) gave the title compound as a brown foam. TLC: rf (1:1 hept-EA)=0.30. LC-MS-conditions 02: tR=1.04 min, [M+H]+=394.37.

Workup

  1. stirringthe reaction mixture was stirred for 16 h at rt
  2. washphase was washed with water (15 mL) and brine (15 mL)
  3. dry with materialphase was then dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (1:1 hept:EA)

Sources & evidence

ORD record
ord-7061723e1cdd42ddbb1b79b54ed394bf
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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