Methanesulfonyl chloride → HCID 58204033, compound

HRID 1849182Notes

Reaction equation

HRID 1849182 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[CH:27]=[CH:26][C:9]3[C:10]4[N:11]=[C:12]([C:18]5[N:19]([CH:23]([CH3:25])[CH3:24])[N:20]=[CH:21][N:22]=5)[S:13][C:14]=4[CH2:15][CH2:16][O:17][C:8]=3[CH:7]=2)[CH2:3]1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>>[CH:23]([N:19]1[C:18]([C:12]2[S:13][C:14]3[CH2:15][CH2:16][O:17][C:8]4[CH:7]=[C:6]([CH:4]5[CH2:5][N:2]([S:29]([CH3:28])(=[O:31])=[O:30])[CH2:3]5)[CH:27]=[CH:26][C:9]=4[C:10]=3[N:11]=2)=[N:22][CH:21]=[N:20]1)([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86652321HCID 86652321, compound

Product 1

HCID 58204033HCID 58204033, compound

Procedure

Following the procedure for 395, 8-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene hydrochloride salt and methanesulfonyl chloride were reacted. The reaction mixture was loaded directly onto a silica column with no aqueous work-up to give 259 isolated as a white solid (67 mg, 84%). LCMS: RT=10.97 min, [M+H]+=446. 1H NMR δ (ppm) (CDCl3): 8.36 (1 H, d, J=8.20 Hz), 7.90 (1 H, d, J=0.68 Hz), 7.16 (1 H, dd, J=8.24, 1.88 Hz), 7.02 (1 H, d, J=1.85 Hz), 5.93-5.83 (1 H, m), 4.42-4.36 (2 H, m), 4.30-4.22 (2 H, m), 4.10-4.03 (2 H, m), 3.83-3.73 (1 H, m), 3.43-3.37 (2 H, m), 2.90 (3 H, s), 1.61 (6 H, d, J=6.63 Hz)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-edbe73427a5c4edfabe84b2b04b96974
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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