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

HRID 528886Notes

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]([I:56])=[CH:52][CH:51]=1)[CH2:46][CH2:47][CH3:48]>>[CH2:45]([N:49]([C:50]1[CH:51]=[CH:52][C:53]([I:56])=[CH:54][CH:55]=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

Reactant 2

HCID 28876905N-Butyl-4-iodoaniline

HCID 71062224HCID 71062224, compound2×

Product 1

HCID 71062241N-Butyl-4-chloro-N-(4-iodophenyl)-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-pyrazole-3-carboxamideYield 41%

Procedure

Following a procedure analogous to that for the synthesis 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, 116 mg, 0.18 mmol) and N-butyl-4-iodoaniline (Okano, K. et al., Org. Lett., 5:4987-4990 (2003)) (59 mg, 0.22 mmol) were converted to the title compound (7 mg, 41%). 1H NMR (MeOD, 1:1 mixture of amide rotamers) δ 8.65 (s, 1H), 8.15-8.07 (m, 1.5H), 8.05-8.00 (m, 3.5H), 7.95 (d, J=8.0 Hz, 1H), 7.69-7.54 (m, 3H), 7.45-7.31 (m, 2H), 7.20-7.17 (m, 4H), 7.03-7.00 (m, 0.5H), 6.97-6.96 (m, 0.5H), 6.70 (d, J=8.6 Hz, 1H), 6.43 (br s, 1H), 4.93 (br s, 0.5H), 4.68 (br s, 0.5H), 4.48 (br s, 0.5H), 4.35 (br s, 0.5H), 3.83 (br s, 1H), 3.71 (br s, 1H), 3.61-3.45 (m, 2H), 3.11-3.01 (m, 1H), 2.92-2.78 (m, 1H), 2.16 (s, 3H), 1.41-1.22 (m, 4H), 0.91-0.80 (m, 3H); MS(ESI+) m/z 886.8 (M+H)+.

Sources & evidence

ORD record: ord-40416378f5a54033bee894d1d7b3d04e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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