Hydrochloric Acid → HCID 16045384, compound

HRID 331205Notes

Reaction equation

HRID 331205 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[C:25]([NH:26][C:27]3[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[CH:28]=3)=[N:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.O.[OH-].[Li+].O.Cl>C1COCC1>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([NH:26][C:25]2[C:16]([NH:15][S:12]([C:9]3[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:37])=[O:2])=[CH:7][CH:8]=3)(=[O:14])=[O:13])=[N:17][C:18]3[C:23]([N:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 16045916HCID 16045916, compound

Product 1

HCID 16045384HCID 16045384, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl-3-{4-[({3-[(3,5-dimethoxyphenyl)amino]quinoxalin-2-yl}amino)sulfonyl]phenyl}propanoate (50 mg, 0.10 mmol, 1 eq.) and lithium hydroxide monohydrate (20.1 mg, 0.48 mmol, 5 eq.) are dissolved in THF (1 ml) and water (1 ml) and the yellow solution is heated up to 50° C. for 1 h. Aqueous HCl 1N is added until reaching acidic pH and the precipitate formed is filtered off then washed with water until neutral. The solid is dried under vacuum at 40° C. overnight, affording 38.1 mg (78%) of the title compound as a yellow powder. 1H NMR (DMSO-d6) δ 12.30-11.95 (m, 2H), 8.91 (s, 1H), 8.02 (d, J=8.2 Hz, 2H), 7.95-7.82 (br s, 1H), 7.60-7.50 (m, 1H), 7.48-7.23 (m, 6H), 6.23 (s, 1H), 3.75 (s, 6H), 2.88 (t, J=7.2 Hz, 2H), 2.56 (t, J=7.5 Hz, 2H). HPLC (max plot) 100%; Rt 4.10 min. LC/MS: (ES+): 509.4; (ES−): 507.4.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. washthen washed with water until neutral
  4. customThe solid is dried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-5b18ef0eaa5f4b2083a0fc21bae45e30
Source dataset
uspto-grants-2014_11
Patent number
US08877757B2

Reaction notes

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