Morpholine → HCID 10051164, compound

HRID 2113074Notes

Reaction equation

HRID 2113074 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([NH:12][C:13]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=4)[N:16]=[CH:15][N:14]=3)=[CH:7][CH:8]=2)[N:3]=1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[ClH:1].[N:29]1([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][C:6]([NH:12][C:13]4[CH:18]=[C:17]([C:19]5[CH:20]=[CH:21][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:23][CH:24]=5)[N:16]=[CH:15][N:14]=4)=[CH:7][CH:8]=3)[N:3]=2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 10023954HCID 10023954, compound

Product 1

HCID 10051164HCID 10051164, compound

Conditions

Temperature
200 °C

Procedure

A solution of (2-chloroquinolin-7-yl)-[6-(4-trifluoromethylphenyl)pyrimidin-4-yl]amine, Example 13(b), (150 mg, 0.37 mmol) in morpholine (0.65 mL, 7.4 mmol, Aldrich) was stirred and heated in a microwave at 200° C. for 10 min. The resulting bright yellow solid was precipitated from EtOAc and CH2Cl2, then dissolved in EtOAc (100 mL) and treated with 1 N HCl (50 mL). The resulting bright yellow precipitate was collected by filtration, washed with water (20 mL), EtOAc (20 mL) and air-dried to provide the title product as a yellow amorphous solid. MS (ESI, pos. ion) m/z: 452 (M+1).

Workup

  1. customThe resulting bright yellow solid was precipitated from EtOAc and CH2Cl2
  2. dissolutiondissolved in EtOAc (100 mL)
  3. additiontreated with 1 N HCl (50 mL)
  4. filtrationThe resulting bright yellow precipitate was collected by filtration
  5. washwashed with water (20 mL), EtOAc (20 mL)
  6. customair-dried

Sources & evidence

ORD record
ord-2f451fcec3734e208b18dfa5a07f539d
Source dataset
uspto-grants-2009_04
Patent number
US07524874B2

Reaction notes

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