Triethylamine → HCID 58777562, compound

HRID 1371720Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[N:3]=1.[CH2:26]1[CH2:33][O:32][S:29](=[O:31])(=[O:30])[CH2:28][CH2:27]1.C(N(CC)CC)C>O1CCCC1>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:21][CH2:22][N:23]([S:29]([CH2:28][CH2:27][CH2:26][CH2:33][OH:32])(=[O:31])=[O:30])[CH2:24][CH2:25]2)[N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

The mixture of [4-amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone (100 mg, 0.290 mmol, Example 59), 1,4-butane sultone (81 uL, 0.870 mmol, Aldrich) and triethylamine (41 uL, 0.290 mmol) in tetrahydrofuran (3 mL) was heated at 150° C. for 1 hour using the Smith Creator microwave synthesizer. Upon cooling to room temperature, the reaction mixture was concentrated. Purification of the crude residue by reverse phase HPLC (C18, eluting with water and acetonitrile) gave [4-amino-2-[1-(4-hydroxy-butane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone as white solids (120 mg, 86%). HR-MS (ES, m/z) calculated for C21H29N5O5SF [(M+H)+] 482.Example 221, observed 482.1874.

Workup

temperatureUpon cooling to room temperature
concentrationthe reaction mixture was concentrated
customPurification of the crude residue
washby reverse phase HPLC (C18, eluting with water and acetonitrile)

Sources & evidence

ORD record: ord-515fc334b3dd4621adde5730b9c4278b
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157455B2

Reaction notes

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