Triethylamine → HCID 51030061, compound

HRID 244516Notes

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

(S)—N-(3-(2-methylpyridin-4-yl)-1H-indazol-5-yl)-3-(methylthio)pyrrolidine-3-carboxamide 6 (176 mg, 0.2 mmol) and 2-chloro-1-(1-(thiazol-2-yl)piperidin-4-yl)ethanone 5 (52 mg, 0.2 mmol) was mixed in DMF (2 mL) together with triethylamine (0.1 mL). The reaction mixture was heated at 45° C. for 3 hrs before concentrated to dryness in vacuo. The resulting crude was purified on silica gel column (eluting with 2% to 4% NH3/MeOH (2 N) in CH2Cl2) to yield 7 as a light yellow solid (89 mg, 77%). LCMS M+1=576.3 retention time=1.73 min.

Workup

concentrationbefore concentrated to dryness in vacuo
customThe resulting crude was purified on silica gel column (eluting with 2% to 4% NH3/MeOH (2 N) in CH2Cl2)

Sources & evidence

ORD record: ord-a11df4a50b4c45549d3bc353bbac89b2
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658651B2

Reaction notes

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