1-Hydroxybenzotriazole → Ethyl{[4-({[(2-butyl-1-benzofuran-3-yl)methyl]amino}carbonyl)-benzyl][4-(trifluoromethyl)benzyl]amino}(oxo)acetate

HRID 735928Notes

Reaction equation

HRID 735928 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C:5]([N:7]([CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:6])[CH3:2].Cl.[CH2:31]([C:35]1[O:36][C:37]2[CH:45]=[CH:44][CH:43]=[CH:42][C:38]=2[C:39]=1[CH2:40][NH2:41])[CH2:32][CH2:33][CH3:34].C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:29])[C:5]([N:7]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:41][CH2:40][C:39]2[C:38]3[CH:42]=[CH:43][CH:44]=[CH:45][C:37]=3[O:36][C:35]=2[CH2:31][CH2:32][CH2:33][CH3:34])=[O:26])=[CH:27][CH:28]=1)[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=1)=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 67186678(2-Butyl-1-benzofuran-3-yl)methylamine hydrochlorideHCID 67187953HCID 67187953, compound

Product 1

HCID 67187715Ethyl{[4-({[(2-butyl-1-benzofuran-3-yl)methyl]amino}carbonyl)-benzyl][4-(trifluoromethyl)benzyl]amino}(oxo)acetateYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The same procedure as employed in the preparation of Example 1 (step d) but using 4-({[ethoxy(oxo)acetyl][4-(trifluoromethyl)benzyl]amino}methyl)benzoic acid and [(2-butyl-1-benzofuran-3-yl)methyl]amine hydrochloride, HOBT and TEA in DCM gave the title compound as a white solid (33%). 1H NMR (CDCl3, 300 MHz) δ 7.66 (m, 2H), 7.51 (m, 3H), 7.35-7.18 (m, 7H), 6.05 (br s, 1H), 4.64 (s, 2H), 4.44 (s, 2H), 4.29 (m, 4H), 2.78 (m, 2H), 1.66 (m, 2H), 1.46 (m, 2H), 1.24 (m, 3H), 0.88 (m, 3H). M−(LC/MS(ESI)): 593; M+(LC/MS(ESI)): 595. HPLC (Condition A), Rt: 6.38 min (HPLC purity: 99.6%).

Workup

  1. customThe same procedure as employed in the preparation of Example 1 (step d)

Sources & evidence

ORD record
ord-600b267083464c9488e1d30fdfb950cf
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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