Methanesulfonyl chloride → HCID 66611597, compound

HRID 709169Notes

Reaction equation

HRID 709169 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[NH2:7][CH:8]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]([F:39])([F:38])[F:37])[CH2:9][NH:10][C:11](=[O:29])[CH2:12][N:13]1[C:17](=[O:18])[N:16]([CH:19]2[CH2:21][CH2:20]2)[C:15]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[N:14]1>N1C=CC=CC=1>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:15]2[N:16]([CH:19]3[CH2:21][CH2:20]3)[C:17](=[O:18])[N:13]([CH2:12][C:11]([NH:10][CH2:9][CH:8]([NH:7][S:2]([CH3:1])(=[O:4])=[O:3])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:38])([F:39])[F:37])=[O:29])[N:14]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride3×HCID 89764675HCID 89764675, compound

Product 1

HCID 66611597HCID 66611597, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At RT, 4.1 μl of methanesulphonyl chloride were added to a solution of 29 mg (48 μmol) of the compound of Example 59A in 0.5 ml of pyridine. The mixture was stirred at RT for 1 h, and another 4.1 ml of methanesulphonyl chloride were added. The mixture was stirred at RT for another 18 h, and another 12.3 μl of methanesulphonyl chloride were added over a period of 3 h (265 μmol, 5.5 eq., in total). After 1 h, the volatile components were removed on a rotary evaporator. The residue was dissolved in a little DMSO and purified by preparative HPLC [Method 9]. This gave 17 mg (65% of theory) of the title compound.

Workup

  1. stirringThe mixture was stirred at RT for another 18 h
  2. waitAfter 1 h
  3. customthe volatile components were removed on a rotary evaporator
  4. dissolutionThe residue was dissolved in a little DMSO
  5. custompurified by preparative HPLC [Method 9]

Sources & evidence

ORD record
ord-08fed0b2f1be407888098d94cb0a5b89
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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