4-(N-Boc-amino)piperidine → HCID 68816915, compound

HRID 2105216Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH:14]=2)[N:5]=[C:4]([NH:24][C:25]2[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=2)[CH:3]=1.[C:31]([O:35][C:36]([NH:38][CH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>O1CCOCC1>[C:31]([O:35][C:36]([NH:38][CH:39]1[CH2:40][CH2:41][N:42]([C:2]2[N:7]=[C:6]([N:8]3[CH2:12][CH2:11][CH2:10][CH:9]3[C:13]3[O:17][N:16]=[C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)[CH:14]=3)[N:5]=[C:4]([NH:24][C:25]3[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=3)[CH:3]=2)[CH2:43][CH2:44]1)=[O:37])([CH3:34])([CH3:32])[CH3:33]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-chloro-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Example 17) (150 mg, 0.35 mmol) and 4-(N-tert-butoxycarbonylamino)piperidine (700 mg, 3.5 mmol) were added to dioxane (4 ml) and heated in a sealed vessel under microwave irradiation at 150° C. for 60 minutes. The crude reaction mixture was purified by reverse phase HPLC using a C18 column eluting with water/acetonitrile/TFA (95:5:0.2 decreasing in polarity to 0:100:0.2). The product containing fractions were passed down an SCX-2 column eluting with methanol and then releasing the product with 2N methanolic ammonia. The solvent was removed by evaporation to give the title compound (134 mg, 64%) as a white solid.

Workup

customThe crude reaction mixture
customwas purified by reverse phase HPLC
washeluting with water/acetonitrile/TFA (95:5:0.2 decreasing in polarity to 0:100:0.2)
additionThe product containing fractions
washeluting with methanol
customThe solvent was removed by evaporation

Sources & evidence

ORD record: ord-1cdfa196a26541d09cd49928b858bdf3
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579349B2

Reaction notes

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