4-Nitrobenzoyl chloride → HCID 178525571, compound

HRID 1028839Notes

Reaction equation

HRID 1028839 reaction equation
C1(C)C=CC(S([O:10][CH2:11][C@H:12]2[CH2:15][C@@H:14]([C:16]3[N:20]4[CH:21]=[CH:22][N:23]=[C:24]([Cl:25])[C:19]4=[CH:18][N:17]=3)[CH2:13]2)(=O)=O)=CC=1.C1(C)C=CC(S([O:36][CH2:37][C@H:38]2[CH2:41][C@H:40]([C:42]3[N:46]4[CH:47]=[CH:48][N:49]=[C:50]([Cl:51])[C:45]4=[CH:44][N:43]=3)[CH2:39]2)(=O)=O)=CC=1.[N+:53]([C:56]1[CH:64]=[CH:63][C:59]([C:60](Cl)=[O:61])=[CH:58][CH:57]=1)([O-:55])=[O:54]>>[N+:53]([C:56]1[CH:57]=[CH:58][C:59]([C:60]([O:10][CH2:11][C@H:12]2[CH2:13][C@@H:14]([C:16]3[N:20]4[CH:21]=[CH:22][N:23]=[C:24]([Cl:25])[C:19]4=[CH:18][N:17]=3)[CH2:15]2)=[O:61])=[CH:63][CH:64]=1)([O-:55])=[O:54].[N+:53]([C:56]1[CH:57]=[CH:58][C:59]([C:60]([O:36][CH2:37][C@H:38]2[CH2:39][C@H:40]([C:42]3[N:46]4[CH:47]=[CH:48][N:49]=[C:50]([Cl:51])[C:45]4=[CH:44][N:43]=3)[CH2:41]2)=[O:61])=[CH:63][CH:64]=1)([O-:55])=[O:54]

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 178427764HCID 178427764, compoundHCID 178427765HCID 178427765, compound

Product 2

HCID 178525571HCID 178525571, compoundHCID 178525572HCID 178525572, compound

Procedure

cis-3-(8-Chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutylmethyl 4-nitrobenzoate and trans-3-(8-Chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutylmethyl 4-nitrobenzoate were prepared according to the general procedure for the preparation for cis-3-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutylmethyl toluene-4-sulfonate and trans-3-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutylmethyl toluene-4-sulfonate, except 4-nitrobenzoyl chloride was used instead of p-toluenesulfonic anhydride.

Sources & evidence

ORD record
ord-ca28979a93dd4787b57d165b5a7fd373
Source dataset
uspto-grants-2014_05
Patent number
US08735405B2

Reaction notes

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