Acetyl chloride → HCID 54670257, compound

HRID 1426945Notes

Reaction equation

HRID 1426945 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[F:5][C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][CH2:24][CH2:23][NH:22][CH2:21][C:20]1=[C:29]3[N:30]=[C:14]([CH:15]=[CH:16][N:17]3[N:18]=[CH:19]1)[N:13]1[C@@H:9]2[CH2:10][CH2:11][CH2:12]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:5][C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][CH2:24][CH2:23][N:22]([C:1](=[O:3])[CH3:2])[CH2:21][C:20]1=[C:29]3[N:30]=[C:14]([CH:15]=[CH:16][N:17]3[N:18]=[CH:19]1)[N:13]1[C@@H:9]2[CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 70168839HCID 70168839, compound

Product 1

HCID 54670257HCID 54670257, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (1.7 mg, 0.021 mmol) was added to a DCM (0.5 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, 5.0 mg, 0.014 mmol), followed by DIEA (7.4 μL, 0.042 mmol). After stirring at ambient temperature overnight, the reaction was concentrated and purified by reverse-phase column chromatography eluting with 0-80% acetonitrile/H2O to provide the title product (3.9 mg, 70% yield). MS (apci) m/z=396.2 (M+H).

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by reverse-phase column chromatography
  3. washeluting with 0-80% acetonitrile/H2O

Sources & evidence

ORD record
ord-1573838dee16403897e8fd338cb73026
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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