Cyclohexylhydrazine hydrochloride → 8-Chloro-2-(2-cyclohexyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulene

HRID 1629449Notes

Reaction equation

HRID 1629449 reaction equation
C[N:2](C)[CH:3]=[N:4][C:5]([C:7]1[N:16]=[C:15]2[N:9]([CH2:10][CH2:11][O:12][C:13]3[CH:20]=[C:19]([Cl:21])[N:18]=[CH:17][C:14]=32)[CH:8]=1)=O.Cl.[CH:24]1([NH:30]N)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>>[Cl:21][C:19]1[N:18]=[CH:17][C:14]2[C:15]3[N:9]([CH2:10][CH2:11][O:12][C:13]=2[CH:20]=1)[CH:8]=[C:7]([C:5]1[N:30]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[N:2]=[CH:3][N:4]=1)[N:16]=3

Participants

3

Reactant 2

HCID 207836Cyclohexylhydrazine hydrochlorideHCID 582048088-Chloro-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulene-2-carboxylic acid 1-dimethylamino-methylideneamide

Product 1

HCID 582046618-Chloro-2-(2-cyclohexyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulene

Procedure

Following the procedures of Example 378, 8-Chloro-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulene-2-carboxylic acid 1-dimethylamino-methylideneamide was reacted with cyclohexylhydrazine hydrochloride to give 8-Chloro-2-(2-cyclohexyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulene (MS(ESI+) 371.2/373.2) which was reacted with L-prolineamide to give 409. MS(ESI+) 449.2.

Sources & evidence

ORD record
ord-ab0c5e8db0f141ae923ccc37f75211a3
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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