Methanesulfonyl chloride → HCID 67606070, compound

HRID 1965215Notes

Reaction equation

HRID 1965215 reaction equation
[C:1]([O:5][C:6](=[O:39])[N:7]([CH:9]([C:11](=[O:38])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[NH:25][CH2:26][CH:27]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:49][S:50](Cl)(=[O:52])=[O:51]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:39])[N:7]([CH:9]([C:11](=[O:38])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[N:25]([S:50]([CH3:49])(=[O:52])=[O:51])[CH2:26][CH:27]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:16])([CH3:17])[CH3:15])[CH3:10])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67606764HCID 67606764, compound

Product 1

HCID 67606070HCID 67606070, compoundYield 107.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of amine 84 (220 mg, 0.4 mmol) in DCM (10 mL) was cooled to 0° C. and treated with DIPEA (0.21 mL, 1.2 mmol) followed by methanesulfonyl chloride (0.03 mL, 0.42 mmol) and DMAP (5 mg, 0.04 mmol). After 2.5 h, the reaction mixture was diluted with DCM, washed successively with 1M HCl, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 85 (271 mg, 100%) as a yellow-colored foam that was used without further purification. 1H NMR (CDCl3, 300 MHz): δ7.08 (q, J=9.3, 18.9 Hz, 1H), 6.86 (br, 1H), 6.76-6.69 (m, 1H), 6.63-6.58 (m, 1H), 4.73-4.65 (m, 1H), 4.60 (d, J=9.6 Hz, 1H), 4.47 (d, J=6.3 Hz, 1H), 4.33-4.29 (m, 1H), 4.16-4.07 (m, 2H), 4.01-3.96 (m, 1H), 3.68-3.53 (m, 3H), 2.93-2.79 (m, 6H), 2.57-2.50 (m, 1H), 2.12-2.06 (m, 1H), 1.61 (s, 1.5H), 1.49 (s, 7.5H), 1.31 (d, J=6.9 Hz, 3H), 0.99 (s, 9H) ppm.

Workup

  1. washwashed successively with 1M HCl, and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e9057444aa2b4f0f9c6c3fa4449842bf
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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