Hydrochloric Acid → HCID 67050564, compound

HRID 1190549Notes

Reaction equation

HRID 1190549 reaction equation
Br[C:2]1[CH:27]=[CH:26][C:5]2[C:6]3[N:7]=[C:8]([C:14]4[N:18]([CH:19]([CH3:21])[CH3:20])[C:17]([C:22]([F:25])([F:24])[F:23])=[N:16][N:15]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.O1CCCCC1[O:34][CH2:35][CH2:36][N:37]1[CH:41]=[C:40](B2OC(C)(C)C(C)(C)O2)[CH:39]=[N:38]1.O1CCCCC1OC1CCCCO1.Cl>>[CH:19]([N:18]1[C:17]([C:22]([F:24])([F:25])[F:23])=[N:16][N:15]=[C:14]1[C:8]1[S:9][C:10]2[CH2:11][CH2:12][O:13][C:4]3[CH:3]=[C:2]([C:40]4[CH:39]=[N:38][N:37]([CH2:36][CH2:35][OH:34])[CH:41]=4)[CH:27]=[CH:26][C:5]=3[C:6]=2[N:7]=1)([CH3:21])[CH3:20]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 263182Tetrahydropyranyl etherHCID 593418191-[2-(oxan-2-yloxy)ethyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67050590HCID 67050590, compound

Product 1

HCID 67050564HCID 67050564, compound

Procedure

Similarly to as described in General Procedure C, 8-bromo-2-(4-isopropyl-5-trifluoromethyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene was reacted with 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. Subsequent to the Suzuki coupling, deprotection of the tetrahydropyranyl ether was accomplished by adding 2N HCl to the crude reaction mixture. Purification by reverse phase HPLC gave 346 as a colorless solid (112 mg). LCMS: 491.1. 1H NMR (400 MHz, DMSO) δ 8.27 (d, J=13.7 Hz, 1H), 8.23 (s, 1H), 7.95 (s, 1H), 7.44 (dd, J=8.3, 1.7 Hz, 1H), 7.32 (d, J=1.7 Hz, 1H), 5.45-5.29 (m, 1H), 4.91 (t, J=5.3 Hz, 1H), 4.41 (t, J=5.0 Hz, 2H), 4.16 (t, J=5.6 Hz, 2H), 3.77 (q, J=5.5 Hz, 2H), 3.48 (t, J=5.0 Hz, 2H), 1.70 (t, J=11.9 Hz, 6H)

Workup

  1. customreaction mixture
  2. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-0aebb4ca60f94ecfb30dae073f3ce47a
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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