Bromoacetic Acid → HCID 70169425, compound

HRID 1426950Notes

Reaction equation

HRID 1426950 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][NH:18][CH2:17][C:16]1=[C:25]3[N:26]=[C:10]([CH:11]=[CH:12][N:13]3[N:14]=[CH:15]1)[N:9]1[C@@H:5]2[CH2:6][CH2:7][CH2:8]1.Br[CH2:28][C:29]([OH:31])=[O:30].[OH-].[Na+]>CC(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][N:18]([CH2:28][C:29]([OH:31])=[O:30])[CH2:17][C:16]1=[C:25]3[N:26]=[C:10]([CH:11]=[CH:12][N:13]3[N:14]=[CH:15]1)[N:9]1[C@@H:5]2[CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 14798Sodium HydroxideHCID 70168839HCID 70168839, compound

Product 1

HCID 70169425HCID 70169425, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

An IPA (0.1 mL) solution of (6R)-9-fluoro-13-oxa-2,16,20,21,24-pentaazapentacyclo-[16.5.2.02,6.07,12.021,25]pentacosa-1(24),7,9,11,18(25),19,22-heptaene (Example 21, 5 mg, 0.014 mmol), 2-bromoacetic acid (2.9 mg, 0.021 mmol) and NaOH (1 N, 42 μL, 0.042 mmol) was heated at 60° C. in a sealed vessel overnight, then at 120° C. for 24 hours. After cooling, the reaction mixture was directly purified by reverse-phase column chromatography eluting with 0-50% acetonitrile/H2O to afford the title product (3.1 mg, 53% yield). MS (apci) m/z=412.2 (M+H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was directly purified by reverse-phase column chromatography
  3. washeluting with 0-50% acetonitrile/H2O

Sources & evidence

ORD record
ord-063749a7bce6413e9ff273de8562630f
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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