Ammonium Chloride → HCID 23584982, compound

HRID 1640173Notes

Reaction equation

HRID 1640173 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]#[N:32])[CH:26]=4)=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].[Cl-].[NH4+:37]>CO>[NH2:32][C:31](=[NH:37])[C:27]1[CH:26]=[C:25]([O:24][C:18]2[CH:17]=[C:16]3[C:21]([CH2:22][CH2:23][CH:14]([C:12]([NH:11][C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=4)=[O:13])[CH2:15]3)=[CH:20][CH:19]=2)[CH:30]=[CH:29][N:28]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 58902223HCID 58902223, compound

Product 1

HCID 23584982HCID 23584982, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(3-tert-butylphenyl)-7-[(2-cyanopyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxamide (1.5 g, 3.5 mmol) in MeOH (20 mL) was added sodium methoxide (28 mg, 0.52 mmol). The solution was allowed to stir at rt for 3 days and then ammonium chloride (0.28 g, 5.3 mmol) was added. The reaction mixture was allowed to stir overnight and then concentrated to give 7-({2-[amino(imino)methyl]pyridin-4-yl}oxy)-N-(3-tert-butylphenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide I-422 as a white solid, which was directly used into the next step. LCMS: (FA) ES+ 443.3.

Workup

  1. stirringto stir overnight
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-17a91f672d60404393bf726065d3503c
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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