Methanesulfonyl chloride → HCID 58203816, compound

HRID 1190598Notes

Reaction equation

Cl.[CH:2]([N:5]1[C:9]([C:10]2[S:11][C:12]3[CH2:13][CH2:14][O:15][C:16]4[CH:23]=[C:22]([CH:24]5[CH2:28][CH2:27][NH:26][CH2:25]5)[CH:21]=[CH:20][C:17]=4[C:18]=3[N:19]=2)=[N:8][CH:7]=[N:6]1)([CH3:4])[CH3:3].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>>[CH:2]([N:5]1[C:9]([C:10]2[S:11][C:12]3[CH2:13][CH2:14][O:15][C:16]4[CH:23]=[C:22]([CH:24]5[CH2:28][CH2:27][N:26]([S:30]([CH3:29])(=[O:32])=[O:31])[CH2:25]5)[CH:21]=[CH:20][C:17]=4[C:18]=3[N:19]=2)=[N:8][CH:7]=[N:6]1)([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 86652322HCID 86652322, compound

Product 1

HCID 58203816HCID 58203816, compound

Procedure

Following the procedure for 395, 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-pyrrolidin-3-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene hydrochloride salt and methanesulfonyl chloride gave 396 isolated as a pale orange solid (28 mg, 48%). LCMS: RT=11.27 min, [M+H]+=460. 1H NMR δ (ppm) (CDCl3): 8.33 (1H, d, J=8.21 Hz), 7.90 (1H, s), 7.05 (1H, dd, J=8.24, 1.91 Hz), 6.94 (1H, d, J=1.87 Hz), 5.93-5.83 (1H, m), 4.42-4.36 (2H, m), 3.79 (1H, dd, J=9.53, 7.31 Hz), 3.61 (1H, ddd, J=9.97, 8.27, 3.30 Hz), 3.50-3.31 (5H, m), 2.86 (3H, s), 2.41-2.32 (1H, m), 2.15-2.03 (1H, m), 1.61 (6H, d, J=6.63 Hz)

Sources & evidence

ORD record: ord-49f52da65a5c4550b8d8cbed6296ec61
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673952B2

Reaction notes

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