Methanesulfonyl chloride → HCID 117728288, compound

HRID 1772602Notes

Reaction equation

HRID 1772602 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:20]=[C:21](/[CH:23]=[CH:24]/[C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[N:22]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:20]=[C:21](/[CH:23]=[CH:24]/[C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[N:22]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([NH:19][S:36]([CH3:35])(=[O:38])=[O:37])=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86346028HCID 86346028, compound

Product 1

HCID 117728288HCID 117728288, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound 8a (200 mg, 0.450 mmol) in pyridine (4 mL) was added methanesulfonyl chloride (150 mg, 1.32 mmol). The resulting solution was stirred in a 10 mL sealed tube at 30° C. for 8 h. The reaction was quenched with H2O (10 mL). The resulting solids were collected by filtration. The crude material was purified by flash column chromatography on silica gel, eluting with DCM/MeOH (100:1 v/v) to obtain compound 8b as a light yellow solid (26.8 mg, 11% yield). 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 10.91 (s, 1H), 8.55 (s, 1H), 8.35 (d, J=8.4 Hz, 1H), 8.23 (s, 1H), 8.12 (d, J=2.4 Hz, 1H), 8.10-7.93 (m, 2H), 7.87 (d, J=4.8 Hz, 1H), 7.83 (d, J=2.7 Hz, 1H), 7.78-7.73 (m, 1H), 7.68-7.54 (m, 2H), 7.44 (s, 1H), 7.17 (d, J=8.7 Hz, 1H), 4.40-4.20 (m, 4H), 3.85-3.75 (m, 4H), 3.39 (s, 3H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C27H25N7O3S: 528.2 (M+H). Found 528.0.

Workup

  1. customsealed tube at 30° C. for 8 h
  2. customThe reaction was quenched with H2O (10 mL)
  3. filtrationThe resulting solids were collected by filtration
  4. customThe crude material was purified by flash column chromatography on silica gel
  5. washeluting with DCM/MeOH (100:1 v/v)

Sources & evidence

ORD record
ord-0611c27f936f49f1b4aa5306b29f07c4
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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