Ammonium Chloride → HCID 178495708, compound

HRID 1475525Notes

Reaction equation

HRID 1475525 reaction equation
[ClH:1].[CH3:2][O:3][CH2:4][C@H:5]1[CH2:10][NH:9][C@H:8]([CH3:11])[CH2:7][N:6]1[CH2:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]#[N:25])[CH:22]=2)[C:17]([CH3:27])([CH3:26])[CH2:16]1)=[O:14].[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+]>CN(C=O)C>[ClH:1].[CH3:27][C:17]1([CH3:26])[C:18]2[C:23](=[CH:22][C:21]([C:24]3[NH:30][N:29]=[N:28][N:25]=3)=[CH:20][CH:19]=2)[N:15]([C:13](=[O:14])[CH2:12][N:6]2[CH2:7][C@@H:8]([CH3:11])[NH:9][CH2:10][C@@H:5]2[CH2:4][O:3][CH3:2])[CH2:16]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 70980867HCID 70980867, compound

Product 1

HCID 178495708HCID 178495708, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1-{2-[(2R,5R)-2-(methoxymethyl)-5-methylpiperazin-1-yl]acetyl}-3,3-dimethyl-2,3-dihydro-1H-indole-6-carbonitrile hydrochloride (25 mg, 0.06 mmol) in DMF (1 mL) was treated with sodium azide (9.0 mg, 0.13 mmol) and ammonium chloride (4.0 mg, 0.06 mmol), and heated under reflux under nitrogen. After 16 h the mixture was filtered and concentrated in vacuo. The residue was purified by preparative HPLC, basic method then treated with a saturated solution of HCl in EtOAc followed by concentration to dryness in vacuo to give the title compound (1.2 mg, 4%). 1H NMR (Me-d3-OD): 8.86-8.78 (1H, m), 7.77 (1H, d), 7.33 (1H, d), 3.95 (1H, d), 3.88 (1H, d), 3.78 (1H, d), 3.68 (1H, d), 3.62-3.46 (2H, m), 3.39-3.33 (3H, m), 3.33 (3H, s), 3.13 (1H, d), 3.07-2.91 (2H, m), 1.49-1.35 (6H, s), 1.29 (3H, d). MS: [M+H]+=400.

Workup

  1. temperatureheated
  2. temperatureunder reflux under nitrogen
  3. filtrationAfter 16 h the mixture was filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC, basic method
  6. additionthen treated with a saturated solution of HCl in EtOAc
  7. concentrationfollowed by concentration to dryness in vacuo

Sources & evidence

ORD record
ord-3d8220d9e30b437e92e14bf1b7543b1b
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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