Ammonium Chloride → HCID 178420480, compound

HRID 1919625Notes

Reaction equation

HRID 1919625 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[C:7]1([NH:13][C:14]2[C:23]3[C:18](=[CH:19][N:20]=[CH:21][CH:22]=3)[C:17]3[CH:24]=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:16]=3[N:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C)C=O.O>[C:7]1([NH:13][C:14]2[C:23]3[C:18](=[CH:19][N:20]=[CH:21][CH:22]=3)[C:17]3[CH:24]=[CH:25][C:26]([C:28]4[NH:29][N:3]=[N:2][N:1]=4)=[CH:27][C:16]=3[N:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 57500636HCID 57500636, compound

Product 1

HCID 178420480HCID 178420480, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Sodium azide (65 mg, 1 mmol) and ammonium chloride (53 mg, 1 mmol) were added to a crude mixture of the 5-(phenylamino)benzo[c][2,6]naphthyridine-8-carbonitrile (25 mg, 0.084 mmol) in dimethylformamide (0.2 mL). The mixture was heated for 18 h at 120° C. at which time LCMS analysis indicated the absence of any starting material. The mixture was diluted with water and purified by preparative HPLC to give N-phenyl-8-(1H-tetrazol-5-yl)benzo[c][2,6]naphthyridin-5-amine (14 mg). LCMS (ESI) 340.3 (M+1)+. 1HNMR (400 MHz, CD3OD) 10.11 (1H, s), 8.96 (1H, d, 5.9 Hz), 8.85 (1H, d, 8.2 Hz), 8.53 (1H, d, 5.5 Hz), 8.47 (1H, s), 8.16 (1H, d, 8.6 Hz), 7.88 (1H, s), 7.86 (1H, d, 0.8 Hz), 7.57-7.51 (3H, m), 7.36-7.31 (2H, m).

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-6443ca6f259a4a6a8749268a4c9ea6f3
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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