HCID 58292630, compound → HCID 58292811, compound

HRID 1798208Notes

Reaction equation

HRID 1798208 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[N:18]=[C:17]([O:19][C:20]2[CH:21]=[C:22]([CH3:34])[C:23]3[CH:27]([CH2:28][C:29]([OH:31])=[O:30])[O:26][B:25]([OH:32])[C:24]=3[CH:33]=2)[CH:16]=[CH:15][N:14]=1)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[N:18]=[C:17]([O:19][C:20]2[CH:21]=[C:22]([CH3:34])[C:23]3[CH:27]([CH2:28][C:29]([OH:31])=[O:30])[O:26][B:25]([OH:32])[C:24]=3[CH:33]=2)[CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 1

HCID 58292630HCID 58292630, compound

Product 1

HCID 58292811HCID 58292811, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of {6-[2-(3-tert-butoxycarbonylamino-propoxy)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.3 g, 0.64 mmol) in 4M HCl in dioxane (3 mL) was stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo and the residue purified by preparative HPLC to give {6-[2-(3-amino-propoxy)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.1 g, 42%). 1H NMR (400 MHz, DMSO): δ 8.46 (d, J=6.0 Hz, 1H), 8.04 (brs, 2H), 7.34 (d, J=2.0 Hz, 1H), 7.12 (d, J=2.0 Hz, 1H), 6.72 (d, J=5.6 Hz, 1H), 5.54 (dd, J=2.0, 9.6 Hz, 1H), 4.28 (t, J=6.0 Hz, 2H), 3.10 (dd, J=2.4 Hz, 15.6 Hz, 1H), 2.88-2.83 (m, 2H), 2.32 (s, 3H), 2.20-2.14 (m, 1H), 2.00-1.97 (m, 2H). MS (ESI) m/z=372 [M−H]−.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-d888a40bf997474393220d263ab88d6f
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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