Morpholine → HCID 178493097, compound

HRID 415414Notes

Reaction equation

HRID 415414 reaction equation
[Cl:1][C:2]1[C:3]([NH:19][C:20]2[CH:24]=[C:23]([O:25][CH3:26])[NH:22][N:21]=2)=[N:4][C:5]([NH:9][C@H:10]([C:12]2[N:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)[CH3:11])=[N:6][C:7]=1Cl.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.CCN(C(C)C)C(C)C>CCCCO>[Cl:1][C:2]1[C:3]([NH:19][C:20]2[CH:24]=[C:23]([O:25][CH3:26])[NH:22][N:21]=2)=[N:4][C:5]([NH:9][C@H:10]([C:12]2[N:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)[CH3:11])=[N:6][C:7]=1[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 178493095HCID 178493095, compound

Product 1

HCID 178493097HCID 178493097, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5,6-dichloro-N2-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-N4-(5-methoxy-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (Example 30, 100 mg), morpholine (0.026 mL) and DIPEA (0.066 ml) in n-BuOH (2.0 ml) was charged into a microwave reaction vessel. The vessel was sealed and heated at 150° C. for 24 hours. The solvent was removed under reduced pressure and the residue was purified by Gilson 2%-40% MeCN/H2O, 15 minutes) to give the titled compound as solid (21.8 mg). 1H NMR δ 11.99 (s, 1H) 9.30 (s, 1H) 8.82 (s, 2H) 7.89 (d, 1H) 5.49 (s, 1H) 4.93-5.14 (m, 1H) 3.75 (s, 3H) 3.44-3.62 (m, 4H) 3.09-3.27 (m, 4H) 1.47 (d, 3H) m/z 450.

Workup

  1. additionwas charged into a microwave reaction vessel
  2. customThe vessel was sealed
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by Gilson 2%-40% MeCN/H2O, 15 minutes)

Sources & evidence

ORD record
ord-8e240b4834f54134874f9f43f88ee403
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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