Hydrochloric Acid → HCID 67252926, compound

HRID 1798200Notes

Reaction equation

HRID 1798200 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][NH: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.[ClH:35]>O1CCOCC1>[ClH:35].[NH2:8][CH2:9][CH2:10][CH2:11][NH: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 2

HCID 313Hydrochloric AcidHCID 67253348HCID 67253348, compound

Product 1

HCID 67252926HCID 67252926, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of {6-[2-(3-tert-butoxycarbonylamino-propylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.27 g, 0.57 mmol) in dioxane (7 mL) was treated with 4N HCl in dioxane (2 mL) at room temperature and stirred for 3 hours at room temperature. The precipitated solid was collected by vacuum filtration, dissolved in water and lyophilized to give {6-[2-(3-amino-propylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid hydrochloride salt as a yellow solid (0.12 g, 56%). 1H NMR (400 MHz, DMSO-d6) δ 8.57 (br s, 1H), 8.37-8.10 (br m, 1H), 7.94 (br m, 3H), 7.50-7.25 (br m, 1H), 7.20-7.05 (br m, 1H), 6.47 (br s, 1H), 5.54 (d, J=9.38 Hz, 1H), 3.36 (br m, 1H), 3.20-3.00 (m, 2H), 2.80 ((m, 1H), 2.67 (m, 1H), 2.33 (s, 3H), 2.20-2.07 (m, 1H), 1.95-1.60 (m, 2H). MS (ESI) m/z: 371 [M−1].

Workup

  1. filtrationThe precipitated solid was collected by vacuum filtration
  2. dissolutiondissolved in water

Sources & evidence

ORD record
ord-9f6119b28314467f81c7084695471a64
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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