Hydrochloric Acid → HCID 118598737, compound

HRID 1050383Notes

Reaction equation

HRID 1050383 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13](F)[N:12]=[CH:11][N:10]=2)[C:5](=[O:16])[N:4]2[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)([CH3:21])[NH:18][C:19](=[O:20])[C:3]=12.[C:29]([NH-:31])#[N:30].[Na+].O.Cl>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:10]=[CH:11][N:12]=[C:13]([NH:31][C:29]#[N:30])[CH:14]=2)[C:5](=[O:16])[N:4]2[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)([CH3:21])[NH:18][C:19](=[O:20])[C:3]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4293993Sodium cyanamideHCID 118598934HCID 118598934, compound

Product 1

HCID 118598737HCID 118598737, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-chloro-3-(3-chlorophenyl)-6-((6-fluoropyrimidin-4-yl)amino)-3-methyl-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione (3, 100 mg, 0.24 mmol) in N-methyl-2-pyrrolidinone (4 mL) was added sodium hydrogencyanamide (46 mg, 0.72 mmol). The reaction was stirred at 50° C. for 2 h. The resulting mixture was cooled to room temperature, poured into water and acidified to pH=5.5 with concentrated hydrochloric acid. The mixture was filtered. The solid crude was purified via HPLC to afford N-(6-((8-chloro-3-(3-chlorophenyl)-3-methyl-1,5-dioxo-1,2,3,5-tetrahydroimidazo[1,5-a]pyridin-6-yl)amino)pyrimidin-4-yl)cyanamide (Cpd. No. 184).

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. customThe solid crude was purified via HPLC

Sources & evidence

ORD record
ord-9e154db99d7249809c9f2cf2556ad68d
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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