Water → HCID 71270115, compound

HRID 1626921Notes

Reaction equation

HRID 1626921 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[CH:27]=[C:26](Cl)[N:25]=[CH:24][N:23]=1)[CH3:20])=[CH:7]2.O.[OH-].[NH4+:31]>O1CCOCC1.[Cl-].[Na+].O>[NH2:31][C:26]1[N:25]=[CH:24][N:23]=[C:22]([NH:21][C@H:19]([C:8]2[N:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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])[CH:27]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14923Ammonium Hydroxide3×HCID 86677061HCID 86677061, compound

Product 1

HCID 71270115HCID 71270115, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

A heavy-wall glass tube with stir bar and FEP-encapsulated-silicone o-ring seal was charged with 77 (ca. 300 mg, 0.73 mmol) in 1,4-dioxane (12 mL) and concentrated ammonium hydroxide solution (10 mL), then sealed tightly and heated at 120° C. After 16 h, more ammonium hydroxide (6 mL) was added and heating continued at 150° C. during 6 h, then 160° C. during 24 h. A third portion of ammonium hydroxide (8 mL) was added and heating continued at 150° C. during 3 days. The reaction mixture was poured into a mixture of water and brine (35 mL each), stirred about 1 h at 0° C., and the resulting precipitate collected by filtration and washed with ice-water. This material was dried in vacuo to give (S)-3-(1-(6-aminopyrimidin-4-ylamino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 78. ESI-MS m/z: 392.15 [M+H]+.

Workup

  1. customsealed tightly
  2. temperatureheating
  3. waitcontinued at 150° C. during 6 h
  4. wait160° C. during 24 h
  5. temperatureheating
  6. waitcontinued at 150° C. during 3 days
  7. stirringstirred about 1 h at 0° C.
  8. filtrationthe resulting precipitate collected by filtration
  9. washwashed with ice-water
  10. customThis material was dried in vacuo

Sources & evidence

ORD record
ord-7bb07cfdcb7c4f0e9b2fec6ba4964698
Source dataset
uspto-grants-2014_07
Patent number
US08785470B2

Reaction notes

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