2-(3-(Butyl(3,4-dichlorobenzyl)carbamoyl)-4-chloro-5-methyl-1H-pyrazol-1-yl)-5-(8-(2-morpholinoethoxy)naphthalen-2-ylsulfonylcarbamoyl)benzoic acid → 1-(2-((S)-3-(Azidomethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(8-(2-morpholinoethoxy)naphthalen-2-ylsulfonylcarbamoyl)phenyl)-N-butyl-4-chloro-N-(3,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxamide

HRID 528947Notes

Reaction equation

[CH2:1]([N:5]([CH2:49][C:50]1[CH:55]=[CH:54][C:53]([Cl:56])=[C:52]([Cl:57])[CH:51]=1)[C:6]([C:8]1[C:12]([Cl:13])=[C:11]([CH3:14])[N:10]([C:15]2[CH:23]=[CH:22][C:21]([C:24](=[O:48])[NH:25][S:26]([C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[C:32]([O:39][CH2:40][CH2:41][N:42]5[CH2:47][CH2:46][O:45][CH2:44][CH2:43]5)[CH:33]=[CH:34][CH:35]=4)[CH:30]=3)(=[O:28])=[O:27])=[CH:20][C:16]=2[C:17](O)=[O:18])[N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[N:58]([CH2:61][C@@H:62]1[CH2:71][C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[CH2:64][NH:63]1)=[N+:59]=[N-:60]>>[N:58]([CH2:61][C@@H:62]1[CH2:71][C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[CH2:64][N:63]1[C:17]([C:16]1[CH:20]=[C:21]([C:24](=[O:48])[NH:25][S:26]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[C:32]([O:39][CH2:40][CH2:41][N:42]4[CH2:43][CH2:44][O:45][CH2:46][CH2:47]4)[CH:33]=[CH:34][CH:35]=3)[CH:30]=2)(=[O:28])=[O:27])[CH:22]=[CH:23][C:15]=1[N:10]1[C:11]([CH3:14])=[C:12]([Cl:13])[C:8]([C:6]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:49][C:50]2[CH:55]=[CH:54][C:53]([Cl:56])=[C:52]([Cl:57])[CH:51]=2)=[O:7])=[N:9]1)=[O:18])=[N+:59]=[N-:60]

Participants

Reactant 2

HCID 710621802-(3-(Butyl(3,4-dichlorobenzyl)carbamoyl)-4-chloro-5-methyl-1H-pyrazol-1-yl)-5-(8-(2-morpholinoethoxy)naphthalen-2-ylsulfonylcarbamoyl)benzoic acid2×

HCID 86718892(S)-3-(Azidomethyl)-1,2,3,4-tetrahydroisoquinoline2×

Product 1

HCID 867189111-(2-((S)-3-(Azidomethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(8-(2-morpholinoethoxy)naphthalen-2-ylsulfonylcarbamoyl)phenyl)-N-butyl-4-chloro-N-(3,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxamideYield 79%

Procedure

Following a procedure analogous to that for the synthesis of Example 91, 2-(3-(butyl(3,4-dichlorobenzyl)carbamoyl)-4-chloro-5-methyl-1H-pyrazol-1-yl)-5-(8-(2-morpholinoethoxy)naphthalen-2-ylsulfonylcarbamoyl)benzoic acid (Intermediate 186B, 17 mg, 0.020 mmol) and (S)-3-(azidomethyl)-1,2,3,4-tetrahydroisoquinoline (Intermediate 92A, 15 mg, 0.079 mmol) were converted to the title compound (16 mg, 79%). MS(ESI+) m/z 1028.1 (M+H)+.

Sources & evidence

ORD record: ord-4f8bcab1614f4e839aa117eccc7131eb
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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