Diisopropylethylamine → HCID 54670346, compound

HRID 407924Notes

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].CCN(C(C)C)C(C)C.Cl[C:38]1[N:43]=[CH:42][C:41]([CH2:44][CH3:45])=[CH:40][N:39]=1>CN(C=O)C>[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[CH2:22][CH2:23][N:24]([C:38]3[N:43]=[CH:42][C:41]([CH2:44][CH3:45])=[CH:40][N:39]=3)[CH2:25][CH2:26]2)[C:16]1=[O:27]

Participants

Conditions

Temperature: 100 °C

Procedure

(S)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-1,4′-bipiperidin-2-one hydrochloride (2.6 g, 6.1 mmol) was dissolved in DMF (30 mL) and DIEA (3.2 mL, 18 mmol) and 2-chloro-5-ethylpyrimidine (1.1 g, 8.0 mmol) were added and heated at 100° C. overnight. The reaction was concentrated and purified over silica gel (25-100% EtOAc in hexanes) to afford (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)-1′-(5-ethylpyrimidin-2-yl)-1,4′-bipiperidin-2-one (1.5 g, 3.1 mmol, 51% yield) as a white solid. Mass spectrum (apci) m/z=494.3 (M+H).

Workup

concentrationThe reaction was concentrated
custompurified over silica gel (25-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-fc46f0940d7d4d489b89d9990fb4b809
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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