Glycolic Acid → HCID 58204440, compound

HRID 1498210Notes

Reaction equation

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

Participants

Reactant 2

HCID 757Glycolic Acid

HCID 58204723HCID 58204723, compound

Product 1

HCID 58204440HCID 58204440, compound

Procedure

Following the procedure for 116, 9-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene was reacted with glycolic acid to give 150 as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.95 (s, 1 H); 7.87 (d, J=2.09 Hz, 1 H); 7.28-7.21 (m, 1 H); 7.24-7.19 (m, 1 H); 6.87 (s, 1 H); 5.68-5.59 (m, 1 H); 4.60-4.48 (m, 4 H); 4.20 (dd, J=9.89, 6.11 Hz, 1 H); 4.16-4.07 (m, 1 H); 4.05 (d, J=3.28 Hz, 2 H); 4.03-3.96 (m, 1 H); 3.18 (t, J=5.91 Hz, 2 H); 1.58 (d, J=6.62 Hz, 6 H). 1 Exchangeable proton not observed. LCMS: RT=8.95 min, M+H+=409

Sources & evidence

ORD record: ord-29ba240528fd44ce88cb1b7b83ba9d2e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198918B2

Reaction notes

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