Hydrochloric Acid → HCID 46187154, compound

HRID 241812Notes

Reaction equation

HRID 241812 reaction equation
Cl.O(C([NH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[C:15]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[O:25])=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)=O)C(C)(C)C>C1COCC1>[ClH:33].[NH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[C:15]([C:24]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[O:25])=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58542474HCID 58542474, compound

Product 1

HCID 46187154HCID 46187154, compoundYield 111%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of HCl (4 N, 2 mL) was added to a stirred solution of 19 (134 mg, 0.29 mmol) in THF (2 mL) at room temperature. The resulting mixture was stirred at room temperature for overnight. The solvent was removed under reduced pressure and the residue was treated with Et2O (2 mL). The precipitate was collected by filtration and washed with dichloromethane to give a white solid (63 mg, 55%): 1H NMR (400 MHz, DMSO-d6) δ 10.66 (s, 1H), 8.17 (s, 1H), 7.97 (d, J=8.4 Hz, 1H), 7.89 (brs, 3H), 7.88 (d, J=8.0 Hz, 1H), 7.80 (d, J=8.0 Hz, 2H), 7.56 (t, J=7.2 Hz, 1H), 7.50 (s, 1H), 7.43 (t, J=6.8 Hz, 1H), 7.43 (d, J=8.8 Hz, 2H), 4.29 (t, J=5.6 Hz, 2H), 2.95-3.03 (m, 2H), 2.10 (quintet, J=6.4 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ 165.1. 152.9, 138.0, 134.8, 129.5, 128.7, 128.2, 127.8, 127.5, 127.2, 127.1, 126.5, 124.5, 121.2, 107.2, 65.5, 36.6, 26.5.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was treated with Et2O (2 mL)
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with dichloromethane

Sources & evidence

ORD record
ord-15e96983a8a7417cab78548d6eb2982c
Source dataset
uspto-grants-2014_02
Patent number
US08653086B2

Reaction notes

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