HCID 58204093, compound → HCID 58204094, compound

HRID 1849414Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH2:8][O:9]C2CCCCO2)[CH:6]=1.[CH:16]([N:19]1[C:23]([C:24]2[S:25][C:26]3[CH2:27][CH2:28][O:29][C:30]4[CH:37]=[C:36](B5OC(C)(C)C(C)(C)O5)[CH:35]=[CH:34][C:31]=4[C:32]=3[N:33]=2)=[N:22][CH:21]=[N:20]1)([CH3:18])[CH3:17]>>[CH:16]([N:19]1[C:23]([C:24]2[S:25][C:26]3[CH2:27][CH2:28][O:29][C:30]4[CH:37]=[C:36]([C:2]5[N:3]=[CH:4][N:5]([CH2:7][CH2:8][OH:9])[CH:6]=5)[CH:35]=[CH:34][C:31]=4[C:32]=3[N:33]=2)=[N:22][CH:21]=[N:20]1)([CH3:18])[CH3:17]

Participants

Reactant 2

HCID 58204093HCID 58204093, compound

HCID 67050657HCID 67050657, compound

Product 1

HCID 58204094HCID 58204094, compound

Procedure

Following the procedure for 258, 4-Bromo-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-imidazole was reacted with 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene to give 486. MS(ESI+) 423.1. 1H NMR (400 MHz, DMSO) δ 8.32 (d, J=8.3, 1H), 8.11 (s, 1H), 7.73 (d, J=1.0, 1H), 7.68 (d, J=0.9, 1H), 7.58 (dd, J=8.3, 1.7, 1H), 7.44 (d, J=1.7, 1H), 5.95-5.74 (m, 1H), 5.00 (t, J=5.2, 1H), 4.39 (t, J=5.0, 2H), 4.03 (t, J=5.4, 2H), 3.70 (q, J=5.3, 2H), 3.44 (t, J=5.0, 2H), 1.56 (d, J=6.6, 6H)

Sources & evidence

ORD record: ord-f8812b952c614cb09298ff24118d25ad
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952043B2

Reaction notes

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