1,2-Dichloroethane → Benzoxazole-6-carboxylic acid (furan-2-ylmethyl)-amide

HRID 1945483Notes

Reaction equation

HRID 1945483 reaction equation
C12(C3C=CC(OC[C:17]4[O:18][C:19]5[CH:25]=[C:24]([C:26]([OH:28])=O)[CH:23]=[CH:22][C:20]=5[N:21]=4)=CC=3)CC3CC(CC(C3)C1)C2.[CH2:31]([NH2:37])[C:32]1[O:36][CH:35]=[CH:34][CH:33]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[O:36]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH2:31][NH:37][C:26]([C:24]1[CH:23]=[CH:22][C:20]2[N:21]=[CH:17][O:18][C:19]=2[CH:25]=1)=[O:28]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 3438FurfurylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 249665352-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-6-carboxylic acid

Product 1

HCID 86637084Benzoxazole-6-carboxylic acid (furan-2-ylmethyl)-amideYield 32.5%

Reagents, catalysts & solvents 1

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolSolvent

Procedure

To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-6-carboxylic acid (30.1 mg, 0.08 mmol), furfuryl amine (11.0 mg, 0.12 mmol, 0.01 ml), EDC (21.7 mg, 0.12 mmol) and HOBt (15.4 mg, 0.12 mmol) in DMF 3.0 mL was added DIPEA (14.2 mg, 0.12 mmol, 0.02 ml). After stirring at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (n-Hexane:EtOAc:MeOH=6:3:1) to give 2-adamantan-1-yl-phenoxymethyl)-benzoxazole-6-carboxylic acid (furan-2-ylmethyl)-amide as a white solid (6.3 mg, 17.4% yield).

Workup

  1. customthe mixture was partitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (n-Hexane:EtOAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-badc8e4ce7444289949d5fc6eaeed883
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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