Methanesulfonyl chloride → HCID 68506957, compound

HRID 2069460Notes

Reaction equation

HRID 2069460 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[C:4]1[N:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19](C)[C:18](OC[C@@H]4CO4)=[C:17](CC)[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:29])[N:5]=1)[CH3:2].[CH3:32][CH2:33][N:34](C(C)C)C(C)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C(Cl)Cl.CCOC(C)=O>[CH2:30]([N:3]([CH2:1][CH3:2])[C:4]1[N:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([CH2:32][CH2:33][NH:34][S:42]([CH3:41])(=[O:44])=[O:43])=[CH:19][CH:20]=3)[N:11]=2)[CH:7]=[C:6]([CH3:29])[N:5]=1)[CH3:31]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86645307HCID 86645307, compound

Product 1

HCID 68506957HCID 68506957, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 12 (100 mg, 0.28 mmol) and DIPEA (97 μL, 0.57 mmol) in DCM (2 mL) at 0° C. is added dropwise a solution of methanesulfonyl chloride (33 μL, 0.43 mmol) in DCM (2 mL). The reaction mixture is stirred at rt for 1 h and is then diluted with EtOAc, and washed with sat. aq. NaHCO3. The org. phase is dried over MgSO4, filtered, evaporated and purified by prep. TLC (eluting with Heptane/EtOAc 1:1) to give the title compound (71 mg) as a yellow solid; LC-MS: tR=1.07 min; [M+H]+=431.07.

Workup

  1. washwashed with sat. aq. NaHCO3
  2. dry with materialphase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by prep
  6. washTLC (eluting with Heptane/EtOAc 1:1)

Sources & evidence

ORD record
ord-6b08d99c98d84ba893efabae1d0d7f6c
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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