Hydrochloric Acid → HCID 58204138, compound

HRID 1190605Notes

Reaction equation

HRID 1190605 reaction equation
Br[C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:7]=[C:8]([C:14]4[N:18]([CH:19]([CH3:21])[CH3:20])[N:17]=[C:16]([NH2:22])[N:15]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.O1CCCCC1[O:31][CH2:32][CH2:33][N:34]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[N:35]1.O1CCCCC1OC1CCCCO1.Cl>>[NH2:22][C:16]1[N:15]=[C:14]([C:8]2[S:9][C:10]3[CH2:11][CH2:12][O:13][C:4]4[CH:3]=[C:2]([C:37]5[CH:36]=[N:35][N:34]([CH2:33][CH2:32][OH:31])[CH:38]=5)[CH:24]=[CH:23][C:5]=4[C:6]=3[N:7]=2)[N:18]([CH:19]([CH3:21])[CH3:20])[N:17]=1

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 67050596HCID 67050596, compound

Product 1

HCID 58204138HCID 58204138, compound

Procedure

Similar to as described in General Procedure C, 5-(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-1-isopropyl-1H-[1,2,4]triazol-3-ylamine 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 403 as a colorless solid (16 mg). LCMS: 438.1

Workup

  1. customreaction mixture
  2. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-7a7166fdb6d148e4a41bc2dc4d2568b3
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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