Hydrochloric Acid → HCID 67252271, compound

HRID 1798198Notes

Reaction equation

HRID 1798198 reaction equation
C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([O:18][C:19]2[CH:20]=[C:21]([CH3:33])[C:22]3[CH:26]([CH2:27][C:28]([OH:30])=[O:29])[O:25][B:24]([OH:31])[C:23]=3[CH:32]=2)[CH:15]=[CH:14][N:13]=1)=O)(C)(C)C.[ClH:34]>O1CCOCC1>[ClH:34].[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([O:18][C:19]2[CH:20]=[C:21]([CH3:33])[C:22]3[CH:26]([CH2:27][C:28]([OH:30])=[O:29])[O:25][B:24]([OH:31])[C:23]=3[CH:32]=2)[CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67252591HCID 67252591, compound

Product 1

HCID 67252271HCID 67252271, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of {6-[2-(2-tert-butoxycarbonylamino-ethylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.21 g, 0.46 mmol) in dioxane (7 mL) was treated with 4N HCl in dioxane (2 mL) at room temperature. The mixture was stirred for 3 hours at room temperature. The precipitated solid was collected by vacuum filtration, dissolved in water and lyophilized to give {6-[2-(2-amino-ethylamino)-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 (0.142 g, 78%). 1H NMR (400 MHz, DMSO-d6) δ 8.57 (br s, 1H), 8.35-8.20 (br m, 1H), 8.02 (br s, 3H), 7.40-7.30 (br m, 1H), 7.15 (br s, 1H), 6.48 (br s, 1H), 5.53 (d, J=9.38 Hz, 1H), 3.36 (br m, 2H), 3.07 (d, J=14.07 Hz, 1H), 2.95-2.70 (m, 2H), 2.30 (s, 3H), 2.14 (m, 1H). MS (ESI) m/z: 357 [M−1]. 1H NMR (400 MHz, CD3OD) δ8.27 (d, J=6.64 Hz, 1H), 7.28 (s, 1H), 7.17 (s, 1H), 6.70 (d, J=6.64 Hz, 1H), 5.68 (dd, J=8.21, 3.13 Hz, 1H), 3.48 (br m, 2H), 3.19 (dd, J=15.63, 2.74 Hz, 1H), 2.98 (br m, 2H), 2.50 (br m, 1H), 2.40 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-21353ada30a64152be2f5a72671447f6
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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