Ammonium Hydroxide → HCID 71273787, compound

HRID 518249Notes

Reaction equation

HRID 518249 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([C@@H:19]([NH:21][C:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][N:25]=[C:24](Cl)[N:23]=1)[CH3:20])=[CH:7]2.[OH-].[NH4+:33]>C1COCC1>[NH2:33][C:24]1[N:23]=[C:22]([NH:21][C@H:19]([C:8]2[N:9]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:10](=[O:12])[C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[Cl:1])[CH3:20])[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][N:25]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86677060HCID 86677060, compound

Product 1

HCID 71273787HCID 71273787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 75 (450 mg, 0.99 mmol) was dissolved in THF (45 mL), treated with concentrated ammonium hydroxide solution (9 mL), and stirred at ambient temperature for 16 h. The solvent was evaporated in vacuo and the residue suspended in water (50 mL) and brine (20 mL), and extracted with DCM (3×35 mL). The combined organic layers were washed with brine (15 mL each), dried over Na2SO4, and concentrated to afford (S)-3-(1-(2-amino-5-nitropyrimidin-4-ylamino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 76, 430 mg (0.99 mmol, quant.). ESI-MS m/z: 437.16 [M+H]+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionbrine (20 mL), and extracted with DCM (3×35 mL)
  3. washThe combined organic layers were washed with brine (15 mL each)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe5d37fb5cc846128f52f081fe96f049
Source dataset
uspto-grants-2015_08
Patent number
US09115141B2

Reaction notes

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