2-(4-Chloro-3-(dipropylamino)-5-methyl-1H-pyrazol-1-yl)-5-(8-chloronaphthalen-2-ylsulfonylcarbamoyl)benzoic acid → 3-((S)-3-(Azidomethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(4-chloro-3-(dipropylamino)-5-methyl-1H-pyrazol-1-yl)-N-(8-chloronaphthalen-2-ylsulfonyl)benzamide

HRID 528956Notes

Reaction equation

HRID 528956 reaction equation
[Cl:1][C:2]1[C:3]([N:34]([CH2:38][CH2:39][CH3:40])[CH2:35][CH2:36][CH3:37])=[N:4][N:5]([C:8]2[CH:16]=[CH:15][C:14]([C:17](=[O:33])[NH:18][S:19]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[C:25]([Cl:32])[CH:26]=[CH:27][CH:28]=4)[CH:23]=3)(=[O:21])=[O:20])=[CH:13][C:9]=2[C:10](O)=[O:11])[C:6]=1[CH3:7].[N:41]([CH2:44][C@@H:45]1[CH2:54][C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH2:47][NH:46]1)=[N+:42]=[N-:43]>>[N:41]([CH2:44][C@@H:45]1[CH2:54][C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH2:47][N:46]1[C:10]([C:9]1[CH:13]=[C:14]([CH:15]=[CH:16][C:8]=1[N:5]1[C:6]([CH3:7])=[C:2]([Cl:1])[C:3]([N:34]([CH2:38][CH2:39][CH3:40])[CH2:35][CH2:36][CH3:37])=[N:4]1)[C:17]([NH:18][S:19]([C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[C:25]([Cl:32])[CH:26]=[CH:27][CH:28]=2)[CH:23]=1)(=[O:21])=[O:20])=[O:33])=[O:11])=[N+:42]=[N-:43]

Participants

3

Reactant 2

HCID 710623862-(4-Chloro-3-(dipropylamino)-5-methyl-1H-pyrazol-1-yl)-5-(8-chloronaphthalen-2-ylsulfonylcarbamoyl)benzoic acid2×HCID 86718892(S)-3-(Azidomethyl)-1,2,3,4-tetrahydroisoquinoline2×

Product 1

HCID 867189133-((S)-3-(Azidomethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(4-chloro-3-(dipropylamino)-5-methyl-1H-pyrazol-1-yl)-N-(8-chloronaphthalen-2-ylsulfonyl)benzamide

Procedure

Following a procedure analogous to that for the synthesis of Example 91, 2-(4-chloro-3-(dipropylamino)-5-methyl-1H-pyrazol-1-yl)-5-(8-chloronaphthalen-2-ylsulfonylcarbamoyl)benzoic acid (Intermediate 193B, 50 mg, 0.083 mmol) and (S)-3-(azidomethyl)-1,2,3,4-tetrahydroisoquinoline (Intermediate 92A, 17 mg, 0.091 mmol) were converted to the title compound. 1H NMR (CDCl3, 2:1 mixture of amide rotamers) δ 9.15 (s, 1H), 8.27-8.13 (m, 1.5H), 8.07-7.80 (m, 2H), 7.72 (d, J=7.5 Hz, 1.5H), 7.61-7.51 (m, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.28-7.11 (m, 3.5H), 7.08-6.98 (m, 1H), 6.94-6.82 (m, 0.5H), 5.34 (d, J=18.5 Hz, 1H), 4.38-3.93 (m, 3H), 3.48-3.36 (m, 2H), 3.32-2.72 (m, 5H), 2.24 (s, 1H), 2.16 (s, 2H), 1.60-1.12 (m, 4H), 0.94-0.62 (m, 6H); MS(ESI+) m/z 773.2 (M+H)+.

Sources & evidence

ORD record
ord-2b39f8203bfc406899c914d144012552
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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