Water → HCID 54669964, compound

HRID 407977Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][C@H:13]1[CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[C:14]1=[O:26].CCN(C(C)C)C(C)C.[Cl:36][C:37]1[N:42]=[CH:41][C:40]([CH2:43][CH3:44])=[CH:39][N:38]=1.O>CN(C=O)C>[ClH:36].[CH2:43]([C:40]1[CH:39]=[N:38][C:37]([N:23]2[CH2:24][CH2:25][CH:20]([N:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C@H:13]([NH:12][C:3]4[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=4[F:1])[C:14]3=[O:26])[CH2:21][CH2:22]2)=[N:42][CH:41]=1)[CH3:44]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (S)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)-1-(piperidin-4-yl)azepan-2-one (0.10 g, 0.26 mmol) and DIEA (0.14 mL, 0.78 mmol) in DMF (2 mL) was added 2-chloro-5-ethylpyrimidine (0.11 g, 0.78 mmol). This mixture stirred at 100° C. for 4 hours in a sealed tube. The mixture was poured into water (50 mL) and extracted into ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The material was purified by column chromatography using 50% to 100% hexanes/ethyl acetate. The HCl salt was made using HCl in ether to give (S)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)azepan-2-one hydrochloride (0.055 g, 0.11 mmol, 43%) (APCI POS 490 M+H).

Workup

extractionextracted into ethyl acetate (3×50 mL)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe material was purified by column chromatography

Sources & evidence

ORD record: ord-b5d472ab5728420c9e276438af40f298
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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