Morpholine → HCID 22347090, compound

HRID 898041Notes

Reaction equation

HRID 898041 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C:32]3[CH:37]=[CH:36][N:35]=[C:34](Cl)[CH:33]=3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)[C:3]=12.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C:32]3[CH:37]=[CH:36][N:35]=[C:34]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[CH:33]=3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)[C:3]=12

Participants

3

Reactant 2

HCID 8083MorpholineHCID 22347315HCID 22347315, compound

Product 1

HCID 22347090HCID 22347090, compound

Conditions

Temperature
100 °C

Procedure

A suspension of N2-{4-[4-amino-1-(2-chloro-4-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide (0.120 g, 0.00023 mol) and morpholine (10 mL) was heated at 100° C. for 6 days. The solvent was removed in vacuo and the residue was slurried in water (25 mL) for 4 hours. The mixture was filtered and the crude solid was purified by preparative RP-HPLC (Rainin C18, 8 mm, 300 A, 25 cm; 35%-80% acetonitrile-0.050 M ammonium acetate over 20 min, 21 ml/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to give N2-{4-[4-amino-1-(2-morpholino-4-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-1-methyl-1H-2-indolecarboxamide (0.048 g, 0.00008 mol) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationThe mixture was filtered
  3. customthe crude solid was purified by preparative RP-HPLC (Rainin C18, 8 mm, 300 A, 25 cm
  4. wait35%-80% acetonitrile-0.050 M ammonium acetate over 20 min
  5. customThe acetonitrile was removed in vacuo

Sources & evidence

ORD record
ord-7bbc7e306cde423499a1c869be49252d
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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