1,1'-Carbonyldiimidazole → HCID 90148569, compound

HRID 1481657Notes

Reaction equation

HRID 1481657 reaction equation
[C:1]([O:5][C:6](=[O:43])[NH:7][C@@H:8]1[C:22](=[O:23])[N:21]2[CH2:24][C@H:25]([OH:27])[CH2:26][C@H:20]2[C:19](=[O:28])[NH:18][C@:17]2([C:30](=[O:39])[NH:31][S:32]([C:35]3([CH3:38])[CH2:37][CH2:36]3)(=[O:34])=[O:33])[CH2:29][C@H:16]2[CH:15]=[CH:14][CH2:13][CH2:12][CH:11]([CH3:40])[CH2:10][C@H:9]1[CH2:41][CH3:42])([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:49]([N:51]2[CH:55]=N[CH:53]=[CH:52]2)=[O:50])C=1.[F:56][C:57]1[CH:65]=CC=[C:62]2[C:58]=1CN[CH2:61]2>>[F:56][C:57]1[CH:58]=[CH:62][CH:61]=[C:53]2[C:65]=1[CH2:55][N:51]([C:49]([O:27][C@H:25]1[CH2:24][N:21]3[C:22](=[O:23])[C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:43])[C@H:9]([CH2:41][CH3:42])[CH2:10][CH:11]([CH3:40])[CH2:12][CH2:13][CH:14]=[CH:15][C@@H:16]4[CH2:29][C@@:17]4([C:30](=[O:39])[NH:31][S:32]([C:35]4([CH3:38])[CH2:36][CH2:37]4)(=[O:33])=[O:34])[NH:18][C:19](=[O:28])[C@@H:20]3[CH2:26]1)=[O:50])[CH2:52]2

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 147958674-fluoro-2,3-dihydro-1H-isoindoleHCID 90127988tert-butyl((2R,6S,7R,13aS,14aR,16aS,Z)-7-ethyl-2-hydroxy-9-methyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate

Product 1

HCID 90148569HCID 90148569, compound

Procedure

A solution of tert-butyl((2R,6S,7R,13aS,14aR,16aS,Z)-7-ethyl-2-hydroxy-9-methyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate (0.062 g, 0.1 mmol) and CDI (0.019 g, 0.120 mmol) was stirred for 6 h. To the solution was added 4-fluoroisoindoline (0.018 g, 0.130 mmol), and then stirred overnight. Concentration gave 80 mg of a crude mixtures (2R,6S,7R,13aS,14aR,16aS,Z)-6-((tert-butoxycarbonyl)amino)-7-ethyl-9-methyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-2-yl 4-fluoroisoindoline-2-carboxylate, which was used as it was.

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-11e9f3a39ca54dab8d0f8ba68304c154
Source dataset
uspto-grants-2016_08
Patent number
US09409943B2

Reaction notes

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