Diisopropylethylamine → HCID 67470532, compound

HRID 407938Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[C:6]([F:13])=[CH:5][C:4]=1[NH:14][C@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:16]1=[O:27].Cl[C:29]1[N:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[CH:31][CH:30]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:35]([C:32]1[CH:31]=[CH:30][C:29]([N:24]2[CH2:23][CH2:22][CH:21]([N:17]3[CH2:18][CH2:19][CH2:20][C@H:15]([NH:14][C:4]4[CH:5]=[C:6]([F:13])[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:8][C:3]=4[F:2])[C:16]3=[O:27])[CH2:26][CH2:25]2)=[N:34][CH:33]=1)(=[O:37])[CH3:36]

Participants

Conditions

Temperature: 100 °C

Procedure

(S)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-1,4′-bipiperidin-2-one hydrochloride (Example 45, Steps A-E; 0.4 g, 0.944 mmol), 1-(6-chloropyridin-3-yl)ethanone (0.220 g, 1.42 mmol) and DIEA (0.523 mL, 2.83 mmol) were dissolved in DMF (5 mL) and heated at 100° C. overnight. The reaction was concentrated and purified over silica gel (50-100% EtOAc in hexanes) to afford (S)-1′-(5-acetylpyridin-2-yl)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-1,4′-bipiperidin-2-one (0.328 g, 0.647 mmol, 68.6% yield) as yellow solid.

Workup

concentrationThe reaction was concentrated
custompurified over silica gel (50-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-dffa7671968941d08b307477900251d0
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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