2-Chlorobenzoic Acid → HCID 19024437, compound

HRID 1033811Notes

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

Participants

Reactant 4

HCID 83742-Chlorobenzoic Acid

HCID 682631,1'-Carbonyldiimidazole

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

HCID 19024453HCID 19024453, compound

Product 1

HCID 19024437HCID 19024437, compound

Procedure

The title compound was prepared from 2-chlorobenzoic acid (2.5 equivalents), CDI (2.5 equiv), 1-[N-butyl-N-[(2'-sulfamoylbiphenyl-4-yl)methyl]carbamoyl]-1,2,3,4-tetrahydroquinoline (from Step B) (1.0 equiv), and DBU (2.5 equiv), according to the procedure of Example 3, Step C, to give an 83% of the desired material after flash chromatography as an off-white solid, mp 80°-82° C.; homogeneous by TLC in 95:5 CH2Cl2 --MeOH; FAB-MS m/e 616 (M+1)+.

Sources & evidence

ORD record: ord-3b16f43e82694d61a9da7906a2372708
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05312820

Reaction notes

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