N-Butyl-3,4-dichloroaniline → N-Butyl-4-chloro-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-N-phenyl-1H-pyrazole-3-carboxamide

HRID 528914Notes

Reaction equation

HRID 528914 reaction equation
[Cl:1][C:2]1[C:3]([C:42]([OH:44])=O)=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:29])[NH:15][S:16]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)(=[O:18])=[O:17])=[CH:10][C:9]=2[C:30]([N:32]2[CH2:41][CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)=[O:31])[C:6]=1[CH3:7].[CH2:45]([NH:49][C:50]1[CH:55]=[CH:54][C:53](Cl)=[C:52](Cl)[CH:51]=1)[CH2:46][CH2:47][CH3:48]>>[CH2:45]([N:49]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:42]([C:3]1[C:2]([Cl:1])=[C:6]([CH3:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:29])[NH:15][S:16]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)(=[O:18])=[O:17])=[CH:10][C:9]=2[C:30]([N:32]2[CH2:41][CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)=[O:31])[N:4]=1)=[O:44])[CH2:46][CH2:47][CH3:48]

Participants

3

Reactant 2

HCID 29276966N-Butyl-3,4-dichloroanilineHCID 71062224HCID 71062224, compound2×

Product 1

HCID 71062239N-Butyl-4-chloro-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-N-phenyl-1H-pyrazole-3-carboxamide

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 122G, 4-chloro-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-pyrazole-3-carboxylic acid (Intermediate 122F, 50 mg, 0.079 mmol) and N-butyl-3,4-dichloroaniline (Aldrich, 10 mg, 0.046 mmol) were converted to the title compound. 1H NMR (1:1 CD3OD:CDCl3, mixture of amide rotamers) δ 8.73 (s, 1H), 8.12-8.00 (m, 4H), 7.97-7.94 (m, 1H), 7.74-7.66 (m, 2H), 7.57 (br s, 1H), 7.46 (br s, 1H), 7.36 (br s, 1H), 7.26-7.19 (m, 4.5H), 7.12-7.10 (m, 0.5H), 7.00 (br s, 1H), 6.73 (br s, 1H), 6.66 (br s, 0.5H), 6.50 (br s, 0.5H), 4.66 (br s, 0.5H), 4.51 (br s, 0.5H), 4.39 (br s, 0.5H), 4.25 (br s, 0.5H), 3.85 (br s, 2H), 3.58 (br s, 2H), 3.13 (br s, 1H), 2.81 (br s, 1H), 2.20-2.16 (m, 3H), 1.38-1.21 (m, 4H), 0.93-0.83 (m, 3H); MS(ESI+) m/z 760.2 (M+H)+.

Sources & evidence

ORD record
ord-305a50723c4544df892261167c27ed52
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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