Ammonium Chloride → HCID 76284627, compound

HRID 929781Notes

Reaction equation

HRID 929781 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:16]=[C:15]([C:17](O)=[O:18])[O:14][N:13]=2)=[N:10][CH:11]=1.[NH4+].[Cl-].Cl.C[N:28](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:16]=[C:15]([C:17]([NH2:28])=[O:18])[O:14][N:13]=2)=[N:10][CH:11]=1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 90202440HCID 90202440, compound2×

Product 1

HCID 76284627HCID 76284627, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[5-(2-Chloro-benzyloxy)-pyridin-2-yl]-isoxazole-5-carboxylic acid (which may be prepared as described in Preparation of Intermediate 10; 220 mg, 0.67 mmol), NH4Cl (71 mg, 1.33 mmol), N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (258 mg, 1.33 mmol), and 1-hydroxybenzotriazole (183 mg, 1.33 mmol) were taken up in THF (8 mL). Diisopropylethylamine (235 μL, 1.33 mmol) was added and the mixture was stirred overnight under nitrogen. The solvent was evaporated and the residue was purified by flash chromatography on silica, eluting with 50% EtOAc/hexanes, to give 3-[5-(2-chloro-benzyloxy)-pyridin-2-yl]-isoxazole-5-carboxylic acid amide (117.5 mg, 53%) as off-white flakes. HRMS Calcd. for C16H13ClN3O3 (M+H)+, 330.0640. Found: 330.0638.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography on silica
  3. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-5c9212978dae4ab6a7d4f333545417ac
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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