Morpholine → HCID 44250770, compound

HRID 1409187Notes

Reaction equation

HRID 1409187 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH:11]3[CH2:13]C3)[CH:10]=[C:6]2[N:5]=[C:4]([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[CH:3]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>CN1C(=O)CCC1>[CH2:11]([C:9]1[CH:10]=[C:6]2[N:5]=[C:4]([NH:14][C:15](=[O:26])[C:16]3[CH:17]=[CH:18][C:19]([C:22]([OH:25])([CH3:23])[CH3:24])=[CH:20][CH:21]=3)[CH:3]=[C:2]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[N:7]2[N:8]=1)[CH3:13]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86652274HCID 86652274, compound

Product 1

HCID 44250770HCID 44250770, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 2 mL microwave vial was placed N-(7-chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2H, 75 mg, 0.21 mmol) and morpholine (36 mg, 0.42 mmol). To the sealed vial was then added NMP (2 ml) and the mixture was then heated in the microwave at 120° C. for 30 minutes. After cooling to room temperature, the reaction mixture was partitioned between brine and EtOAc. The aqueous layer was extracted once more with EtOAc, and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by recrystallization from ether and EtOAC to give the titled compound (43 mg, 50% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ=10.87 (s, 2H), 8.05-7.92 (m, 2H), 7.59 (d, J=8.6 Hz, 2H), 7.36 (s, 1H), 6.19 (s, 1H), 5.18 (s, 1H), 3.91-3.79 (m, 4H), 3.77-3.69 (m, 4H), 2.74 (q, J=7.6 Hz, 2H), 1.45 (s, 6H), 1.35-1.23 (m, 3H); ESI-MS: m/z 410 (M+H)+.

Workup

  1. customthe reaction mixture was partitioned between brine and EtOAc
  2. extractionThe aqueous layer was extracted once more with EtOAc
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by recrystallization from ether and EtOAC

Sources & evidence

ORD record
ord-56de343af39e4f6e8a7e413a0f778279
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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