Diisopropylethylamine → 1-methyl-3-pentyl-1-[2-(trifluoromethyl)phenyl]-3-[[2'(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]urea

HRID 1033819Notes

Reaction equation

HRID 1033819 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]([F:15])([F:14])[F:13])[C:3](Cl)=[O:4].[CH2:16]([NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[N:39]([C:40]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:38]=[N:37][N:36]=2)=[CH:25][CH:24]=1)[CH2:17][CH2:18][CH2:19][CH3:20].C(N(CC)C(C)C)(C)C>>[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]([F:15])([F:14])[F:13])[C:3]([N:21]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[N:39]([C:40]([C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:38]=[N:37][N:36]=2)=[CH:25][CH:24]=1)=[O:4]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 19024425pentyl[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]amineHCID 19024472N-methyl-N-[2-(trifluoromethyl)phenyl]carbamoyl chloride

Product 1

HCID 190244521-methyl-3-pentyl-1-[2-(trifluoromethyl)phenyl]-3-[[2'(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]ureaYield 26%

Procedure

Following the procedure of Example 7, Step B, N-methyl-N-[2-(trifluoromethyl)phenyl]carbamoyl chloride (from Example 7, Step A) was reacted with 1.2 equivalents of N-pentyl-N-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]amine (from Step D) in the presence of N,N-diisopropylethylamine. Flash chromatography of the crude product on silica gel (elution with 4:1 and then 3:1 hexane-EtOAc) gave two major products. Concentration of fractions containing the pure second product afforded a 26% yield of the title compound as a stiff foam, homogeneous by TLC in 3:1 EtOAc); FAB-MS m/e 772 (M+Li)+. The 1H NMR spectrum indicated the presence of two isomeric forms.

Workup

  1. washFlash chromatography of the crude product on silica gel (elution with 4:1
  2. custom3:1 hexane-EtOAc) gave two major products
  3. additionConcentration of fractions containing the pure second product

Sources & evidence

ORD record
ord-93f9e7ec258e494aaa822cb036b0a1ca
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

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