Hydrochloric Acid → HCID 178520733, compound

HRID 220145Notes

Reaction equation

HRID 220145 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][C:21](O)=[O:22])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[CH:4]=1.[OH-:26].[Na+].Cl.[NH2:29]O.Cl>CO>[OH:26][NH:29][C:21](=[O:22])[CH2:20][C@H:17]1[CH2:16][CH2:15][C@H:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[NH:6][N:7]=[C:3]([C:2]([F:1])([F:24])[F:25])[CH:4]=3)=[CH:9][CH:10]=2)[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 178525542HCID 178525542, compound

Product 1

HCID 178520733HCID 178520733, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A scintillation vial was charged with the product from Example 28 (38 mg, 0.1 mmol), sodium hydroxide (40 mg, 0.1 mmol), hydroxylamine hydrochloride (33 mg, 0.1 mmol) and 4 mL of methanol. The reaction vial was placed in a shaker at room temperature overnight. After this time, the mixture was acidified with 10% HCl, concentrated, and purified on a RP-HPLC to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.10 (m, 2H), 1.48 (m, 2H), 1.67-1.85 (m, 5H), 1.88 (d, J=6.75 Hz, 2H), 2.47 (m, 1H), 7.12 (s, 1H), 7.34 (d, J=8.28 Hz, 2H), 7.72 (d, J=8.24 Hz, 2H), 8.63 (br s, 1H), 10.34 (s, 1H), 13.96 (br s, 1H); MS (ESI) m/z 366.1 [M−H]+.

Workup

  1. customThe reaction
  2. concentrationconcentrated
  3. custompurified on a RP-HPLC

Sources & evidence

ORD record
ord-3505c84251ce47c8ad4daaed86847fa3
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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