Methanesulfonyl chloride → HCID 117728965, compound

HRID 2200045Notes

Reaction equation

HRID 2200045 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[CH:22]=[CH:23][C:24]4[N:25]([C:27]([N:30]5[C@H:35]([CH3:36])[CH2:34][CH2:33][CH2:32][C@@H:31]5[CH3:37])=[N:28][N:29]=4)[CH:26]=3)[CH2:16][CH2:15]2)=[O:12])[N:7]([C:38]2[CH:39]=[N:40][N:41]([CH2:43][CH2:44][OH:45])[CH:42]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:46][S:47](Cl)(=[O:49])=[O:48].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[CH:22]=[CH:23][C:24]4[N:25]([C:27]([N:30]5[C@H:31]([CH3:37])[CH2:32][CH2:33][CH2:34][C@@H:35]5[CH3:36])=[N:28][N:29]=4)[CH:26]=3)[CH2:16][CH2:15]2)=[O:12])[N:7]([C:38]2[CH:39]=[N:40][N:41]([CH2:43][CH2:44][O:45][S:47]([CH3:46])(=[O:49])=[O:48])[CH:42]=2)[N:6]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 117729157HCID 117729157, compound

Product 1

HCID 117728965HCID 117728965, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Intermediate 17b (0.75 g, 1.21 mmol), methanesulfonyl chloride (140 μL, 1.81 mmol) and DIPEA (0.63 mL, 3.62 mmol) in DCM (15 mL) was stirred at RT for 1 h. The reaction mixture was partitioned between DCM and water. The organic layer was washed with brine, separated through a phase separating cartridge and concentrated in vacuo to afford the title compound (0.82 g, 97%). LCMS (Method 3): Rt 3.59 min, m/z 697 [MH+].

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. washThe organic layer was washed with brine
  3. customseparated through a phase
  4. customseparating cartridge
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66d7d1ec194d408db898b22e3bb62eed
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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