Hydrochloric Acid → HCID 69423902, compound

HRID 916853Notes

Reaction equation

HRID 916853 reaction equation
[OH:1][C@H:2]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH2:34][OH:35])[CH:28]=1)[CH2:3][NH:4][CH2:5][CH2:6][C:7]1[CH:26]=[CH:25][C:10]([O:11][CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([NH2:21])=[O:20])=[CH:9][CH:8]=1.[ClH:36]>C(O)(C)C>[ClH:36].[OH:1][C@H:2]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([CH2:34][OH:35])[CH:28]=1)[CH2:3][NH:4][CH2:5][CH2:6][C:7]1[CH:26]=[CH:25][C:10]([O:11][CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([NH2:21])=[O:20])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10217473HCID 10217473, compound

Product 1

HCID 69423902HCID 69423902, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 3-[(2-{4-[2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)ethyl]phenoxy}ethoxy)methyl]benzamide (25 mg) in iso-propanol (0.45 ml) was added hydrochloric acid (12M, 5.1 μl). A heat-cool cycle was applied between 0° C. and 40° C., and the mixture agitated for 90 h. The precipitate was filtered to give the title compound (20 mg). Mp 151- 153° C.; 1H NMR δ (CD3OD, 400 MHz) 7.88 (1H, br s), 7.78 (1H, br d, J 8 Hz), 7.55 (1H, d, J 8 Hz), 7.43 (1H, t, J 8 Hz), 7.34 (1H, br d, J 2 Hz), 7.22-7.13 (3H, m), 6.92 (2H, br d, J 8 Hz), 6.77 (1H, d, J 8 Hz), 4.65 (4H, d, J 7 Hz), 4.16-4.11 (2H, br t, J 4 Hz), 3.87-3.81 (2H, br t, J 4 Hz), 3.27-3.20 (2H, br t, J 8 Hz), 2.98-2.90 (2H, m).

Workup

  1. customwas applied between 0° C. and 40° C.
  2. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-40655cd2482f44e9a979e46f5c87b865
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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