4-Cyanobenzoic acid → HCID 21968624, compound

HRID 1107988Notes

Reaction equation

HRID 1107988 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[N:2].Cl.[CH3:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[C:17]([O:24][CH2:25][C:26]3[C:27]([Cl:48])=[C:28]([S:33]([N:36]4[CH2:40][CH2:39][CH2:38][C@H:37]4[C:41]([NH:43][CH2:44][CH2:45][CH2:46][NH2:47])=[O:42])(=[O:35])=[O:34])[CH:29]=[CH:30][C:31]=3[Cl:32])[CH:18]=[CH:19][CH:20]=2)[N:15]=1>>[CH3:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[C:17]([O:24][CH2:25][C:26]3[C:27]([Cl:48])=[C:28]([S:33]([N:36]4[CH2:40][CH2:39][CH2:38][C@H:37]4[C:41]([NH:43][CH2:44][CH2:45][CH2:46][NH:47][C:7]([C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=4)=[O:9])=[O:42])(=[O:34])=[O:35])[CH:29]=[CH:30][C:31]=3[Cl:32])[CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

3

Reactant 2

HCID 120874-Cyanobenzoic acidHCID 21968625HCID 21968625, compound

Product 1

HCID 21968624HCID 21968624, compoundYield 75%

Procedure

By following a procedure analogous to Example 5, starting from 4-cyanobenzoic acid and 1-[[3-[(2-methylquinolin-8-yl)oxymethyl]-2,4-dichlorophenyl]sulfonyl]-N-[3-aminopropyl]-2(S)-pyrrolidinecarboxamide hydrochloride, the expected product (yield=75%) is obtained after purification by chromatography on silica gel using a dichloromethane/methanol mixture (98/2; v/v) as the eluent. M.p.=78-80° C. [α]D24 =-39° (c=0.3; CH3OH)

Sources & evidence

ORD record
ord-559f9629b869403c8b8a831a86d1b26c
Source dataset
uspto-grants-2000_05
Patent number
US06063791

Reaction notes

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