2-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol → 4-{8-[1-(2-Hydroxy-2-methyl-propyl)-1H-pyrazol-4-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl}-2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one

HRID 2385990Notes

Reaction equation

HRID 2385990 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:5]2[C:6]3[N:7]=[C:8]([N:14]4[C:18]([CH3:19])=[N:17][N:16]([CH:20]([CH3:22])[CH3:21])[C:15]4=[O:23])[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.IC1C=CC2C3N=C(N4C(C)=NN(C(C)C)C4=O)SC=3CCOC=2C=1.[CH3:51][C:52]([OH:69])([CH3:68])[CH2:53][N:54]1[CH:58]=[C:57](B2OC(C)(C)C(C)(C)O2)[CH:56]=[N:55]1>>[OH:69][C:52]([CH3:68])([CH3:51])[CH2:53][N:54]1[CH:58]=[C:57]([C:2]2[CH:25]=[CH:24][C:5]3[C:6]4[N:7]=[C:8]([N:14]5[C:18]([CH3:19])=[N:17][N:16]([CH:20]([CH3:22])[CH3:21])[C:15]5=[O:23])[S:9][C:10]=4[CH2:11][CH2:12][O:13][C:4]=3[CH:3]=2)[CH:56]=[N:55]1

Participants

4

Reactant 3

HCID 582041312-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-olHCID 670505364-(8-Iodo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-oneHCID 670505674-(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one

Product 1

HCID 582037004-{8-[1-(2-Hydroxy-2-methyl-propyl)-1H-pyrazol-4-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl}-2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one

Procedure

Following the procedure for 473, a mixture of 4-(8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one and 4-(8-iodo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one and 2-methyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-propan-2-ol were reacted to give 474 isolated as a white solid (34 mg, 59%). LCMS: RT=4.79 min, [M+H]+=481. 1 H NMR δ (ppm) (DMSO-d6): 8.15 (1 H, d, J=8.26 Hz), 8.08 (1 H, s), 7.87 (1 H, d, J=0.74 Hz), 7.33 (1 H, dd, J=8.26, 1.84 Hz), 7.22 (1H, d, J=1.82 Hz), 4.68 (1 H, s), 4.38-4.28 (3 H, m), 3.99 (2 H, s), 3.28 (2 H, m), 2.67 (3 H, s), 1.29 (6 H, t, J=6.68 Hz), 1.05 (6 H, s)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-fc9e6d908c7d4adf951c6932cd11b12e
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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