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

HRID 1189443Notes

Reaction equation

HRID 1189443 reaction equation
N#N.[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[C:7]([C:9]([OH:11])=O)[N:8]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.Cl.[NH2:51][C:52]1[N:53]=[C:54]([CH2:57][C:58]2[O:62][C:61]([C:63](=[O:65])[CH3:64])=[CH:60][CH:59]=2)[S:55][CH:56]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:63]([C:61]1[O:62][C:58]([CH2:57][C:54]2[S:55][CH:56]=[C:52]([NH:51][C:9]([C:7]3[N:8]=[C:4]([CH3:3])[O:5][C:6]=3[C:12]3[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=3)=[O:11])[N:53]=2)=[CH:59][CH:60]=1)(=[O:65])[CH3:64]

Participants

9

Reactant 6

HCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 669292052-Methyl-5-(m-tolyl)oxazole-4-carboxylic acidHCID 671287161-[5-(4-Amino-thiazol-2-ylmethyl)-furan-2-yl]-ethanone hydrochloride

Product 1

HCID 671284202-Methyl-5-m-tolyl-oxazole-4-carboxylic acid [2-(5-acetyl-furan-2-ylmethyl)-thiazol-4-yl]-amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-methyl-5-m-tolyl-oxazole-4-carboxylic acid (50 mg, 0.23 mmol) in CH2Cl2 (2.3 mL) was treated sequentially with DMAP (7 mg, 0.06 mmol), HOBt (37 mg, 0.28 mmol), EDC.HCl (110 mg, 0.58 mmol) and DIPEA (0.16 mL, 0.92 mmol) and the resulting mixture was stirred at rt for 1 h. This solution was then treated with 1-[5-(4-amino-thiazol-2-ylmethyl)-furan-2-yl]-ethanone hydrochloride (51 mg, 0.23 mmol) 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 an orange oil. TLC: rf (1:1 hept-EA)=0.28. LC-MS-conditions 02: tR=1.11 min, [M+H]+=421.93.

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-22ac98430af141d8aaa82bdb306beb28
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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