Triethylamine → HCID 57896481, compound

HRID 1025786Notes

Reaction equation

HRID 1025786 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@@H:6]1[CH2:10][CH2:9][N:8]([CH:11]2[CH2:16][CH2:15][C:14]([OH:23])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13][CH2:12]2)[CH2:7]1)=[O:4].CCN(CC)CC.Cl[C:32]1[S:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=1>C(O)(C)C>[S:33]1[C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=[C:32]1[NH:1][CH2:2][C:3]([NH:5][C@@H:6]1[CH2:10][CH2:9][N:8]([CH:11]2[CH2:12][CH2:13][C:14]([OH:23])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:15][CH2:16]2)[CH2:7]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 119872-ChlorobenzothiazoleHCID 66787661HCID 66787661, compound

Product 1

HCID 57896481HCID 57896481, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

The mixture of 2-amino-N-[(3R)-1-(4-hydroxy-4-pyridin-2-ylcyclohexyl)pyrrolidin-3-yl]acetamide (0.080 g, 0.25 mmol), Et3N (0.35 mL, 2.5 mmol) and 2-chloro-benzothiazole (0.424 g, 2.5 mmol) in isopropanol was stirred overnight at 90° C. The reaction mixture was concentrated and chromatographed to provide 55 mg of the title compound in 49% yield. MS (EI) calculated: (M+H)+=452.2; found: 452.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed

Sources & evidence

ORD record
ord-4ea4bbd8b1f54bef9139ff63cd1df7ed
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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