Hydrochloric Acid → HCID 86643316, compound

HRID 1672243Notes

Reaction equation

HRID 1672243 reaction equation
[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([NH:13][C:14]2[N:15]=[CH:16][C:17]3[CH2:18][C:19](=[S:33])[NH:20][C:21]4[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:22]=4[C:23]=3[N:24]=2)[C:9]([CH3:12])=[N:10][CH:11]=1.[ClH:35]>C(O)C>[ClH:35].[CH3:34][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([NH:13][C:14]2[N:15]=[CH:16][C:17]3[CH2:18][C:19](=[S:33])[NH:20][C:21]4[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:22]=4[C:23]=3[N:24]=2)[C:9]([CH3:12])=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 462359222-({5-[3-(Dimethylamino)propyl]-2-methylpyridin-3-yl}amino)-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepine-6-thione

Product 1

HCID 86643316HCID 86643316, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-({5-[3-(Dimethylamino)propyl]-2-methylpyridin-3-yl}amino)-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepine-6-thione (131.0 g, 269 mmol) in 200 P ethanol (1.05 L) was heated to reflux. A solution formed. Hydrochloric acid (1.25 M in ethanol, 43 mL, 53.8 mmol) was added slowly. Seeds were added. More hydrochloric acid (1.25 M in ethanol, 172 mL, 215 mmol) was added dropwise over 4 hours. The suspension formed was kept at reflux for 1 hour, then allowed to cool down to room temperature in 5 hours. The product was collected by filtration then washed with EtOH (20 mL). Drying under vacuo at 35° C. overnight afforded 2-({5-[3-(Dimethylamino)propyl]-2-methylpyridin-3-yl}amino)-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepine-6-thione Monohydrochloride Salt as a light yellow solid (128 g, HPLC purity>99%, 90.9% yield). LCMS (FA): Rt=6.08 min, m/z 485.2 (M−H). FTIR: 1575, 1434, 1408, 1334, 1315, 1173, 1136, 1116, 1087, 787 cm−1.

Workup

  1. temperaturewas heated to reflux
  2. customA solution formed
  3. additionSeeds were added
  4. customThe suspension formed
  5. temperatureat reflux for 1 hour
  6. filtrationThe product was collected by filtration
  7. washthen washed with EtOH (20 mL)
  8. customDrying under vacuo at 35° C. overnight

Sources & evidence

ORD record
ord-e6580efd03f7478bb8a9a4cde7a08eec
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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