Methanesulfonyl chloride → HCID 10167256, compound

HRID 1370959Notes

Reaction equation

HRID 1370959 reaction equation
[NH2:1][C:2]1[C:3]([CH3:38])=[C:4]([N:8]([CH2:16][C:17]2[CH:37]=[CH:36][C:20]([O:21][C:22]3[CH:23]=[C:24]([CH:33]=[CH:34][CH:35]=3)[O:25][CH2:26][C@H:27]3[NH:31][C:30](=[O:32])[CH2:29][CH2:28]3)=[CH:19][CH:18]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>N1C=CC=CC=1>[CH2:9]([N:8]([CH2:16][C:17]1[CH:37]=[CH:36][C:20]([O:21][C:22]2[CH:35]=[CH:34][CH:33]=[C:24]([O:25][CH2:26][C@@H:27]3[CH2:28][CH2:29][C:30](=[O:32])[NH:31]3)[CH:23]=2)=[CH:19][CH:18]=1)[C:4]1[C:3]([CH3:38])=[C:2]([NH:1][S:40]([CH3:39])(=[O:42])=[O:41])[CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68857586HCID 68857586, compound

Product 1

HCID 10167256HCID 10167256, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The dried product from example 278B was dissolved in anhydrous pyridine (3 mL) at 0° C. for 30 minutes. Then methanesulfonyl chloride (50 μL, 6 mmoles) was injected. The reaction mixture was let to stand at room temperature for 3 hours. Then the reaction mixture was dried in vaccuo, dissolved in CH2Cl2 (4 mL), filtered and dried in vaccuo. The final residue was purified by HPLC to provide the titled compound. 1H NMR (500 MHz, DMSO-d6) δ8.95 (s, 1 H), 7.76 (s, 1 H), 7.27 (m, 7 H), 7.20 (m, 1 H), 7.04 (m, 1 H), 6.95 (m, 4 H), 6.71 (m, 1 H), 6.53 (m, 2 H), 4.06 (s, 2 H), 4.03 (s, 2 H), 3.92 (m, 1 H), 3.82 (m, 2 H), 2.91 (s, 3 H), 2.39 (s, 3 H), 2.04-2.29 (m, 3 H), 1.80 (m, 1 H); MS (APCI+) m/z 586 (M+H)+.

Workup

  1. customThen the reaction mixture was dried in vaccuo
  2. dissolutiondissolved in CH2Cl2 (4 mL)
  3. filtrationfiltered
  4. customdried in vaccuo
  5. customThe final residue was purified by HPLC

Sources & evidence

ORD record
ord-e966dbd4fcf94c3c98b56c4ae9194853
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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