Benzoic Acid → HCID 22558468, compound

HRID 984438Notes

Reaction equation

HRID 984438 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:12][C:13](=[O:30])[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[O:27][CH:26]=[N:25][CH:24]=3)=[C:19]([O:28][CH3:29])[CH:18]=2)=[O:15])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[C:31](O)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N1CCOCC1)C>ClCCl>[C:31]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:12][C:13](=[O:30])[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[O:27][CH:26]=[N:25][CH:24]=3)=[C:19]([O:28][CH3:29])[CH:18]=2)=[O:15])([CH3:10])[CH3:11])=[CH:4][CH:3]=1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22558446HCID 22558446, compound

Product 1

HCID 22558468HCID 22558468, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 30 mg (0.074 mmol) of N-[2-(4-aminophenyl)-1,1-dimethylethyl]-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide, 10 mg (0.082 mmol) of benzoic acid, 14 mg (0.092 mmol) of 1-hydroxybenzotriazole hydrate, 21 mg (0.11 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 18 mg (0.16 mmol) of N-ethylmorpholine in 2 ml of dichloromethane was stirred at room temperature for 18 hours then diluted with dichloromethane and washed with 2M hydrochloric acid and saturated sodium bicarbonate. The organic phase was dried over magnesium sulphate, evaporated to dryness and the residue chromatographed on silica gel using ethyl acetate/petrol (2:1) for the elution. There was obtained 9 mg of N-[2-(4-benzamidophenyl)-1,1-dimethylethyl]-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide as a white solid. MS: m/e 513 [M+H]+.

Workup

  1. washwashed with 2M hydrochloric acid and saturated sodium bicarbonate
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. customevaporated to dryness
  4. customthe residue chromatographed on silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-26237ff15e924065a0148e65979a3cb7
Source dataset
uspto-grants-2005_03
Patent number
US06867299B2

Reaction notes

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