2-Chlorobenzoic Acid → HCID 19024450, compound

HRID 1033808Notes

Reaction equation

HRID 1033808 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:23]([N:28]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[S:54](=[O:57])(=[O:56])[NH2:55])=[CH:44][CH:43]=1)[C:29]([N:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33][CH2:32]1)=[O:30])[CH2:24][CH2:25][CH2:26][CH3:27].C1CCN2C(=NCCC2)CC1>>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:55][S:54]([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=1[C:45]1[CH:44]=[CH:43][C:42]([CH2:41][N:28]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:29]([N:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34][CH2:33][CH2:32]2)=[O:30])=[CH:47][CH:46]=1)(=[O:57])=[O:56])=[O:6]

Participants

5

Reactant 4

HCID 83742-Chlorobenzoic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19024426HCID 19024426, compound

Product 1

HCID 19024450HCID 19024450, compound

Procedure

The title compound was prepared from 2-chlorobenzoic acid (2.0 equivalents), CDI (2.0 equiv), 1-[N-pentyl-N-[(2'-sulfamoylbiphenyl-4-yl)methyl]carbamoyl]-1,2,3,4-tetrahydroquinoline (from Step B) (1.0 equiv), and DBU (2.0 equiv), according to the procedure of Example 3, Step C, to give a 78% yield of the desired material after flash chromatography as an off-white solid, mp 71°-74° C.; homogeneous by TLC in 9:1 CH2Cl2 --MeOH; FAB-MS m/e 630 (M+1)+.

Sources & evidence

ORD record
ord-2f3864a6f0cb4822b2857ae956cb3a6d
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

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