Dichloromethane → HCID 86691738, compound

HRID 1426949Notes

Reaction equation

HRID 1426949 reaction equation
C(Cl)Cl.[F:4][C:5]1[CH:6]=[C:7]2[C:25](=[CH:26][CH:27]=1)[O:24][CH2:23][CH2:22][NH:21][CH2:20][C:19]1=[C:28]3[N:29]=[C:13]([CH:14]=[CH:15][N:16]3[N:17]=[CH:18]1)[N:12]1[C@@H:8]2[CH2:9][CH2:10][CH2:11]1.CCN(C(C)C)C(C)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>CO>[F:4][C:5]1[CH:6]=[C:7]2[C:25](=[CH:26][CH:27]=1)[O:24][CH2:23][CH2:22][N:21]([S:40]([CH3:39])(=[O:42])=[O:41])[CH2:20][C:19]1=[C:28]3[N:29]=[C:13]([CH:14]=[CH:15][N:16]3[N:17]=[CH:18]1)[N:12]1[C@@H:8]2[CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 70168839HCID 70168839, compound

Product 1

HCID 86691738HCID 86691738, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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 mg, 0.0141 mmol) was added DIEA (2.46 μL, 0.0141 mmol), followed by methanesulfonyl chloride (1.10 μL, 0.0141 mmol). The reaction was stirred at ambient temperature for 1 hour before MeOH (0.1 mL) was added. The reaction was concentrated and purified by reverse-phase column chromatography eluting with 0-80% acetonitrile/H2O to provide the title product (3.1 mg, 50.8% yield). MS (apci) m/z=432.3 (M+H).

Workup

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

Sources & evidence

ORD record
ord-de3ea3431381448896219197ae75a205
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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