Diisopropylethylamine → 1-[N-Pentyl-N-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]carbamoyl]-1,2,3,4-tetrahydroquinoline

HRID 1033817

Reaction equation

HRID 1033817 reaction equation
[N:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:14]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[N:37]([C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:36]=[N:35][N:34]=2)=[CH:23][CH:22]=1)[CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)C(C)C)(C)C>>[CH2:14]([N:19]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[N:37]([C:38]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:36]=[N:35][N:34]=2)=[CH:25][CH:26]=1)[C:11]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:12])[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 135910691,2,3,4-Tetrahydroquinoline-1-carbonyl chlorideHCID 19024425pentyl[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]amine

Product 1

HCID 190244351-[N-Pentyl-N-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]carbamoyl]-1,2,3,4-tetrahydroquinolineYield 27%

Procedure

Following the procedure of Example 7, Step B, 1,2,3,4-tetrahydroquinoline-1-carbonyl chloride (from 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 27% yield of the title compound as a stiff foam, homogeneous by TLC in 3:1 hexane-EtOAc; FAB-MS m/e 723 (M+1)+. 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. addition(Concentration of fractions containing the pure second product

Sources & evidence

ORD record
ord-2f4b341ea6dc4738acee2f571c175677
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Linked notes

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