Triethylamine → HCID 23725909, compound

HRID 2219361Notes

Reaction equation

HRID 2219361 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=2)[CH:17]=1.C(N=C=NCCCN(C)C)C.O[N:39]1[C:43]2[CH:44]=[CH:45][CH:46]=CC=2N=N1.C1(CN)CC1.C(N(CC)CC)C>CN(C=O)C>[CH:44]1([CH2:43][NH:39][C:22](=[O:24])[C:21]2[CH:20]=[CH:19][C:18]([N:16]3[CH:17]=[C:13]([C:3]4[C:4]([C:7]5[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=5)=[N:5][O:6][C:2]=4[CH3:1])[N:14]=[CH:15]3)=[CH:26][CH:25]=2)[CH2:46][CH2:45]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 75646CyclopropanemethanamineHCID 757711-HydroxybenzotriazoleHCID 67420918HCID 67420918, compound

Product 1

HCID 23725909HCID 23725909, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[4-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazol-1-yl]-benzoic acid (100 mg, 0.29 mmol) in DMF (2 mL), was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (85.9 mg, 0.45 mmol) and N-hydroxybenzotriazole (60.7 mg, 0.45 mmol), followed by adding cyclopropylmethylamine (26 mg, 0.36 mmol) and triethylamine (75 mg, 0.75 mmol). The reaction mixture was stirred at room temperature overnight. Purification by preparative HPLC on reversed phase eluting with an acetonitrile/water [0.1% aq NH3 (25%)] gradient afforded the title compound (14 mg, 13%) which was obtained as a white solid. MS m/e=398.9 [M+H]+.

Workup

  1. customPurification by preparative HPLC on reversed phase
  2. washeluting with an acetonitrile/water [0.1% aq NH3 (25%)] gradient

Sources & evidence

ORD record
ord-b838601c3fe344a088467bb62bbd8a54
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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