2-Bromoacetamide → HCID 58204164, compound

HRID 1849285Notes

Reaction equation

OC(C(F)(F)F)=O.[CH:8]([N:11]1[C:15]([C:16]2[S:17][C:18]3[CH2:19][CH2:20][O:21][C:22]4[CH:29]=[CH:28][C:27]([CH:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)=[CH:26][C:23]=4[C:24]=3[N:25]=2)=[N:14][CH:13]=[N:12]1)([CH3:10])[CH3:9].Br[CH2:37][C:38]([NH2:40])=[O:39]>>[CH:8]([N:11]1[C:15]([C:16]2[S:17][C:18]3[CH2:19][CH2:20][O:21][C:22]4[CH:29]=[CH:28][C:27]([CH:30]5[CH2:35][CH2:34][N:33]([CH2:37][C:38]([NH2:40])=[O:39])[CH2:32][CH2:31]5)=[CH:26][C:23]=4[C:24]=3[N:25]=2)=[N:14][CH:13]=[N:12]1)([CH3:10])[CH3:9]

Participants

Reactant 2

HCID 696322-Bromoacetamide

HCID 86652315HCID 86652315, compound

Product 1

HCID 58204164HCID 58204164, compound

Procedure

Following the procedure for 319, 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-9-piperidin-4-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt was alkylated with bromoacetamide to give 357 isolated as a white solid (167 mg, 86%). LCMS: RT=7.55 min, [M+H]+=453. 1H NMR δ (ppm) (DMSO-d6): 8.23 (1 H, d, J=2.30 Hz), 8.06 (1 H, s), 7.14 (1 H, dd, J=8.34, 2.37 Hz), 7.10 (2 H, s), 6.95 (1 H, d, J=8.26 Hz), 5.79-5.68 (1 H, m), 4.33-4.27 (2 H, m), 3.41-3.35 (2 H, m), 2.92-2.81 (4 H, m), 2.50 (1 H, m), 2.17 (2 H, dd, J=12.36, 10.20 Hz), 1.78 (2 H, d, J=12.48 Hz), 1.73-1.61 (2 H, m), 1.53 (6 H, d, J=6.61 Hz)

Sources & evidence

ORD record: ord-b0911221b2254aa5ba20d0ea7c4923f3
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952043B2

Reaction notes

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