Ammonia → HCID 58789219, compound

HRID 708800Notes

Reaction equation

HRID 708800 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[C:15](Cl)=[N:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:28].C([O-])(O)=O.[Na+]>C(O)CO>[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[C:15]([NH2:28])=[N:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 516892Sodium BicarbonateHCID 118093001HCID 118093001, compound

Product 1

HCID 58789219HCID 58789219, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
165 °C

Procedure

To a steel bomb charged with N,N-dibenzyl-1-chloro-7-fluoroisoquinolin-6-amine (3.953 g, 10.49 mmol, see WO 2007/002313 for preparation) was added 15 mL of 7N NH3 in ethylene glycol (prepared by condensing ammonia in ethylene glycol) and the reaction sealed and heated at 165° C. overnight (20 h). The reaction mixture was poured into sat. NaHCO3 (200 mL) and extracted with DCM (3×200 mL). The combined organics were washed with brine (150 mL) and dried (Na2SO4), filtered and concentrated to leave Intermediate 4A (3.71 g, 99% yield) as a yellow solid. MS (ESI) m/z: 358.1 [M+1]+.

Workup

  1. customthe reaction sealed
  2. extractionextracted with DCM (3×200 mL)
  3. washThe combined organics were washed with brine (150 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-012123384b0345f79fcfd1aa8110b61e
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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