Methanesulfonyl chloride → HCID 87085233, compound

HRID 709150Notes

Reaction equation

HRID 709150 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[NH2:7][CH:8]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]([F:43])([F:42])[F:41])[CH2:9][NH:10][C:11](=[O:33])[CH2:12][N:13]1[C:17](=[O:18])[N:16]([CH2:19][C@H:20]([OH:25])[C:21]([F:24])([F:23])[F:22])[C:15]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[N:14]1>N1C=CC=CC=1>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([C:15]2[N:16]([CH2:19][C@H:20]([OH:25])[C:21]([F:23])([F:24])[F:22])[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:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]([F:41])([F:42])[F:43])=[O:33])[N:14]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 89764326HCID 89764326, compound

Product 1

HCID 87085233HCID 87085233, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At RT, 13 μl of methanesulphonyl chloride were added to a solution of 90 mg (0.15 mmol) of the compound of Example 56A in 1.5 ml of pyridine. The mixture was stirred at RT for 1 h, and another 12 ml of methanesulphonyl chloride were added (0.32 mmol, 2.1 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 8]. This gave 59 mg (61% of theory) of the title compound.

Workup

  1. waitAfter 1 h
  2. customthe volatile components were removed on a rotary evaporator
  3. dissolutionThe residue was dissolved in a little DMSO
  4. custompurified by preparative HPLC [Method 8]

Sources & evidence

ORD record
ord-ae6003c457864a2c8cdbcef23ddef5aa
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

Loading…