Norborn-2-ylacetic acid → HCID 69187940, compound

HRID 448038

Reaction equation

HRID 448038 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([OH:11])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[I-].[CH2:46]([N+:50]1[N:54]=[C:53]([CH3:55])[S:52][C:51]=1[CH3:56])[CH2:47][CH2:48][CH3:49]>>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9](/[CH:56]=[C:51]1\[S:52][C:53]([CH3:55])=[N:54][N:50]\1[CH2:46][CH2:47][CH2:48][CH3:49])=[O:11]

Participants

5

Reactant 4

HCID 79139Norborn-2-ylacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 691879173-Butyl-2,5-dimethyl-1,3,4-thiadiazol-3-ium iodide

Product 1

HCID 69187940HCID 69187940, compound

Procedure

In a 20 mL vial 2-(bicyclo[2.2.1]heptan-2-yl)acetic acid (0.9 mL of 0.2 M in DMA, 1.10 equiv) was added followed by the addition of HATU (77 mg in 0.7 mL of DMA, 0.2 mmol, 1.20 equiv.), DIEA (53 mg in 0.7 mL of DMA, 0.4 mmol, 2.40 equiv.), and finally 3-butyl-2,5-dimethyl-1,3,4-thiadiazol-3-ium iodide (50 mg in 0.7 mL of DMA, 0.17 mmol, 1 equiv.). The mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.90 (t, 3H) 0.98-1.18 (m, 4 H) 1.23-1.49 (m, 6 H) 1.62-1.73 (m, 2 H) 1.80-1.88 (m, 1 H) 1.89-1.95 (m, 1 H) 2.11-2.19 (m, 2 H) 2.23-2.31 (m, 1 H) 2.38-2.43 (m, 3 H) 4.02 (t, 2 H) 5.86-5.92 (m, 1 H); MS (ESI) m/z 307 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-f15e509d56184c7ab9958b1ac95539bd
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Linked notes

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