Ammonia → HCID 76287210, compound

HRID 1748728Notes

Reaction equation

HRID 1748728 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[S:15][CH2:14][CH2:13][N:12]([CH2:16][C:17](OC)=[O:18])[C:11]2[N:21]([CH3:30])[N:22]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[C:10]1=2.[C-]#[N:32].[K+].N>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[S:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]([NH2:32])=[O:18])[C:11]2[N:21]([CH3:30])[N:22]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[C:10]1=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 9032Potassium CyanideHCID 86724075HCID 86724075, compound

Product 1

HCID 76287210HCID 76287210, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of methyl 2-[4-(2,4-dichlorophenyl)-1-methyl-3-(2-pyridyl)-6,7-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepin-8-yl]acetate (0.350 g, 0.76 mmol, Preparation #12 step A), KCN (0.050 g, 0.77 mmol), and ammonia (10 mL, 7 M in MeOH, 70 mmol) in methanol (10 mL) was heated, in a sealed flask, for about 50 min at about 140° C. in a microwave. After cooling to rt the mixture was concentrated in vacuo. The residue was purified by column chromatography (SiO2, ethyl acetate/methanol 95:5) to give 2-[4-(2,4-dichlorophenyl)-1-methyl-3-(2-pyridyl)-6,7-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepin-8-yl]acetamide (0.16 g, 0.36 mmol, 47%) as a beige solid: LC-MS (Table 1, Method b) Rt=5.49 min; m/z 448 (M+H)+.

Workup

  1. temperatureAfter cooling to rt the mixture
  2. concentrationwas concentrated in vacuo
  3. customThe residue was purified by column chromatography (SiO2, ethyl acetate/methanol 95:5)

Sources & evidence

ORD record
ord-1a93769e36504dd38f5f0c42a781d02d
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

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