Methanol → HCID 58204886, compound

HRID 886409Notes

Reaction equation

HRID 886409 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21](O)[N:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH3:24][OH:25].[OH2:26]>>[OH:25][C@@H:24]1[CH2:2][CH2:1][N:4]([C:21]2[N:20]=[CH:19][C:16]3[C:17]4[N:11]([CH:10]=[C:9]([C:8]5[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][N:7]=5)[N:18]=4)[CH2:12][CH2:13][O:14][C:15]=3[CH:22]=2)[C@@H:8]1[C:9]([NH2:18])=[O:26]

Participants

4

Reactant 3

HCID 887MethanolHCID 962WaterHCID 1360309132-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol

Product 1

HCID 58204886HCID 58204886, compoundYield 6%

Procedure

Following the procedures of Example 339, 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol from Example 93 and 3-cis-hydroxy-L-prolinamide were reacted and the crude product subjected to RPHPLC (C18 column, gradient 15 to 55% methanol in water+0.1% HCO2H) to give 397 as a white powder (11 mg, 6%). LCMS: RT=2.28 min, [M+H]+ 425. 1H NMR 400 MHz (DMSO-d6) δ: 9.08 (1H, s), 7.91 (1H, d, J=0.63 Hz), 7.85 (1H, s), 7.20 (1H, br), 6.94 (1H, br), 6.00-5.98 (1H, m), 5.94 (1H, s), 5.25 (1H, d, J=4.81 Hz), 4.51-4.50 (4H, m), 4.47 (1H, m), 4.27 (1H, m), 3.68 (1H, m), 3.41 (1H, m), 2.09-2.08 (1H, m), 2.04-2.01 (1H, m), 1.50 (6H, dd, J=6.59, 3.26 Hz)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-11b216ac5442468faa3008a77f82de36
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

Loading…