Hydrochloric Acid → HCID 68772375, compound

HRID 1172334Notes

Reaction equation

HRID 1172334 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15]C)=[O:14])=[C:5]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH2:4][C@H:3]1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33].O1CCCC1.O.[Li+].[OH-].Cl>CCOCC>[NH2:1][C@@H:2]1[CH2:7][C:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[C:5]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH2:4][C@H:3]1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21881883Oxolane--water (1/1)HCID 68768163HCID 68768163, compound

Product 1

HCID 68772375HCID 68772375, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of Example 9B (18 mg, 0.037 mmol) in mixture of tetrahydrofuran/H2O (0.5 mL/0.25 mL), LiOH (9.4 mg, 0.22 mmol) was added at room temperature. The reaction mixture was stirred overnight. It was acidified with 2N HCl in ether until the pH=3 and purified by reverse-phase high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (14 mg, 80%). 1H NMR (500 MHz, methanol-d4) δ ppm 8.65-8.76 (m, 2H), 8.25-8.33 (m, 1H), 7.81-7.91 (m, 1H), 7.48-7.65 (m, 3H), 7.30-7.44 (m, 3H), 7.01-7.10 (m, 1H), 4.48-4.59 (m, 2H), 4.00-4.12 (m, 1H), 3.74-3.87 (m, 1H), 2.60-3.02 (m, 4H). MS (ESI) m/z 469 (M+H)+.

Workup

  1. additionwas added at room temperature
  2. custompurified by reverse-phase high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-fa6d358392d048e083ac82aced5ba09d
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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