Methanesulfonyl chloride → HCID 54670531, compound

HRID 1426951Notes

Reaction equation

HRID 1426951 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:8]=[C:9]2[C:28](=[CH:29][CH:30]=1)[O:27][CH2:26][CH2:25][CH2:24][NH:23][CH2:22][C:21]1=[C:31]3[N:32]=[C:15]([CH:16]=[CH:17][N:18]3[N:19]=[CH:20]1)[N:14]1[C@@H:10]2[CH2:11][CH2:12][CH2:13]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:6][C:7]1[CH:8]=[C:9]2[C:28](=[CH:29][CH:30]=1)[O:27][CH2:26][CH2:25][CH2:24][N:23]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:22][C:21]1=[C:31]3[N:32]=[C:15]([CH:16]=[CH:17][N:18]3[N:19]=[CH:20]1)[N:14]1[C@@H:10]2[CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 70168482HCID 70168482, compound

Product 1

HCID 54670531HCID 54670531, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (1.69 μL, 0.0218 mmol) was added to a DCM (0.5 mL) solution of (6R)-9-fluoro-13-oxa-2,17,21,22,25-pentaazapentacyclo[17.5.2.02,6.07,12.022,26]hexacosa-1(25),7,9,11,19(26),20,23-heptaene (Example 24, 4.0 mg, 0.0109 mmol), followed by DIEA (9.48 μL, 0.0544 mmol). The reaction was stirred at ambient temperature overnight, concentrated and purified by reverse-phase column chromatography eluting with 0-80% acetonitrile/H2O to afford the title compound (2.9 mg, 59.8% yield). MS (apci) m/z=446.3 (M+H).

Workup

  1. concentrationconcentrated
  2. custompurified by reverse-phase column chromatography
  3. washeluting with 0-80% acetonitrile/H2O

Sources & evidence

ORD record
ord-c5b514c3b2804a5facfac0eb0e8b0fef
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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