Ammonium Chloride → HCID 178479677, compound

HRID 1418586Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]([F:39])([F:38])[C:7]1[CH:8]=[C:9]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]#[N:20])[CH2:14][C@H:13]1[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)=[O:11].[Cl-:40].[NH4+]>CN(C)C=O>[ClH:40].[F:38][C:6]([F:5])([F:39])[C:7]1[CH:8]=[C:9]([CH:31]=[C:32]([C:34]([F:36])([F:35])[F:37])[CH:33]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[NH:20][N:3]=[N:2][N:1]=2)[CH2:14][C@H:13]1[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)=[O:11]

Participants

Conditions

Temperature: 115 °C

Procedure

Sodium azide (0.21 g) was added to a stirred mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(cyanomethyl)-2-(1H-indol-3-yl-methyl)piperazine (0.32 g) and ammonium chloride (0.17 g) in dimethylformamide (5 ml). The mixture was stirred at 115° C. for 16 hours. Additional sodium azide and ammonium chloride were added to the reaction mixture until the starting material was consumed. After cooling, the mixture was poured into ice-cold water. The resulting precipitate was collected by filtration, washed with water and dried. The precipitate was treated with 4N hydrogen chloride in dioxane solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)-4-(1H-tetrazol-5-yl-methyl)piperazine hydrochloride (0.19 g).

Workup

customwas consumed
temperatureAfter cooling
additionthe mixture was poured into ice-cold water
filtrationThe resulting precipitate was collected by filtration
washwashed with water
customdried
additionThe precipitate was treated with 4N hydrogen chloride in dioxane solution

Sources & evidence

ORD record: ord-a8a459479f0d4b00b75be739b9da69e6
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05883098

Reaction notes

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