4-(1,2,3,4-Tetrahydroquinoline-1-sulfonyl)benzoic acid → HCID 178521759, compound

HRID 1482815Notes

Reaction equation

HRID 1482815 reaction equation
[N:1]1([S:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:34]=[C:33]([NH2:35])[NH:32][N:31]=2)=[CH:26][CH:25]=1>>[N:1]1([S:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH:35][C:33]3[NH:32][N:31]=[C:30]([C:27]4[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=4)[CH:34]=3)=[O:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 23189394-(1,2,3,4-Tetrahydroquinoline-1-sulfonyl)benzoic acidHCID 178507289HCID 178507289, compound

Product 1

HCID 178521759HCID 178521759, compound

Procedure

4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzoic acid (1) (100 mg, 0.32 mmol) was treated with 3-(4-fluorophenyl)-1H-pyrazol-5-amine (43 mg, 0.24 mmol) using method B. The residue was purified using flash chromatography eluting with 0-8% MeOH in EtOAc. The resulting solid was triturated with dichloromethane/hexanes to give 4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)-N-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)benzamide as an off white solid. Yield: 36 mg (31%). 1H-NMR: 11.11 (s, 1H), 8.10 (d, J=8.5 Hz, 2H), 7.80 (dd, J=8.5, 5.5 Hz, 2H), 7.71 (d, J=8.0 Hz, 2H), 7.62 (d, J=8.5 Hz, 1H), 7.33-7.08 (m, 5H), 7.01 (br s, 1H), 3.83-3.79 (m, 2H), 2.45 (t, J=7.0 Hz, 2H), 1.66-1.58 (m, 2H).

Workup

  1. customThe residue was purified
  2. washeluting with 0-8% MeOH in EtOAc
  3. customThe resulting solid was triturated with dichloromethane/hexanes

Sources & evidence

ORD record
ord-b8925c4f0b6f496aac1afe6ef1a8f8a8
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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