Triethylamine → HCID 58203757, compound

HRID 2385958Notes

Reaction equation

HRID 2385958 reaction equation
[OH:1][C:2]([C:4](F)(F)F)=O.[NH:8]1[CH2:11][CH:10]([C:12]2[CH:33]=[CH:32][C:15]3[C:16]4[N:17]=[C:18]([C:24]5[N:25]([CH:29]([CH3:31])[CH3:30])[N:26]=[CH:27][N:28]=5)[S:19][C:20]=4[CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)[CH2:9]1.ClCC[S:37](Cl)(=[O:39])=[O:38].C(N(CC)CC)C>>[CH:29]([N:25]1[C:24]([C:18]2[S:19][C:20]3[CH2:21][CH2:22][O:23][C:14]4[CH:13]=[C:12]([CH:10]5[CH2:11][N:8]([S:37]([CH2:4][CH2:2][OH:1])(=[O:39])=[O:38])[CH2:9]5)[CH:33]=[CH:32][C:15]=4[C:16]=3[N:17]=2)=[N:28][CH:27]=[N:26]1)([CH3:31])[CH3:30]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 866523168-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 TFA salt

Product 1

HCID 58203757HCID 58203757, compound

Procedure

Following the procedure for 394, 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 TFA salt 235, 2-chloroethanesulfonyl chloride, and 1.0 equivalents of triethylamine were reacted to give 445. LCMS: RT=8.49 min, [M+H]+=476. 1H NMR δ (ppm) (DMSO-d6): 8.29 (1H, d, J=8.20 Hz), 8.06-8.03 (1H, m), 7.22 (1H, dd, J=8.27, 1.86 Hz), 7.13 (1 H, d, J=1.82 Hz), 5.82-5.72 (1 H, m), 4.36-4.26 (4 H, m), 4.10-3.94 (3H, m), 3.45-3.35 (4 H, m), 2.72-2.65 (2 H, m), 1.50 (6 H, d, J=6.59 Hz). 1 Exchangeable proton not seen

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-981f666c569a4714bba5228e6dd34db9
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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