3-Aminobenzonitrile → HCID 66761752, compound

HRID 1397946Notes

Reaction equation

HRID 1397946 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.[NH2:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[C:27]#[N:28]>>[C:27]([C:26]1[CH:25]=[C:24]([NH:23][C:18](=[O:20])[C:17]2[CH:16]=[CH:15][C:14]([S:11]([N:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH2:4][CH2:3][CH2:2]3)(=[O:13])=[O:12])=[CH:22][CH:21]=2)[CH:31]=[CH:30][CH:29]=1)#[N:28]

Participants

3

Reactant 2

HCID 167023-AminobenzonitrileHCID 23189394-(1,2,3,4-Tetrahydroquinoline-1-sulfonyl)benzoic acid

Product 1

HCID 66761752HCID 66761752, compound

Procedure

4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzoic acid (1) (100 mg, 0.32 mmol) was treated with 3-aminobenzonitrile (29 mg, 0.24 mmol) using method B. The residue was purified using flash chromatography eluting with 0-30% EtOAc in hexanes. The resulting solid was triturated with dichloromethane/hexanes to give N-(3-cyanophenyl)-4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzamide as a white solid. Yield: 12 mg (12%). 1H-NMR: 10.76 (s, 1H), 8.23-8.20 (m, 1H), 8.07 (d, J=8.5 Hz, 2H), 8.03-7.98 (m, 1H), 7.77 (d, J=8.5 Hz, 2H), 7.63 (d, J=8.5 Hz, 1H), 7.61-7.58 (m, 2H), 7.23-7.18 (m, 1H), 7.11-7.07 (m, 2H), 3.85-3.80 (m, 2H), 2.45 (t, J=7.0 Hz, 2H), 1.68-1.59 (m, 2H).

Workup

  1. customThe residue was purified
  2. washeluting with 0-30% EtOAc in hexanes
  3. customThe resulting solid was triturated with dichloromethane/hexanes

Sources & evidence

ORD record
ord-c997533d4d3d442dbcb73087a08c32e6
Source dataset
uspto-grants-2014_12
Patent number
US08901306B2

Reaction notes

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