Hydrochloric Acid → HCID 58204260, compound

HRID 1190666Notes

Reaction equation

C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[C:19]([C:20]3[S:21][C:22]4[CH2:23][CH2:24][O:25][C:26]5[CH:33]=[C:32]([C:34]6[CH:35]=[N:36][N:37]([CH2:39][C:40]([CH3:43])([OH:42])[CH3:41])[CH:38]=6)[CH:31]=[CH:30][C:27]=5[C:28]=4[N:29]=3)=[N:18][CH:17]=[N:16]2)[CH2:11][CH2:10]1)(C)(C)C.CO.Cl>>[OH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[C:19]([C:20]3[S:21][C:22]4[CH2:23][CH2:24][O:25][C:26]5[CH:33]=[C:32]([C:34]6[CH:35]=[N:36][N:37]([CH2:39][C:40]([CH3:43])([OH:42])[CH3:41])[CH:38]=6)[CH:31]=[CH:30][C:27]=5[C:28]=4[N:29]=3)=[N:18][CH:17]=[N:16]2)[CH2:11][CH2:10]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 67050607HCID 67050607, compound

Product 1

HCID 58204260HCID 58204260, compoundYield 25.1%

Procedure

To a solution of 1-{4-[2-(2-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-piperidin-4-yl}-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-pyrazol-1-yl}-2-methyl-propan-2-ol (0.150 g, 0.000231 mol) in methanol (2.0 mL, 0.049 mol) was added hydrogen chloride (4N in dioxane, 1 mL, 0.00025 mol). The reaction was stirred at room temperature overnight. The solvent was removed in vacuo and the crude was purified by reverse-phase HPLC to give 462 (31.1 mg) as a white solid. MS (ESI+) 536.2

Workup

customThe solvent was removed in vacuo
customthe crude was purified by reverse-phase HPLC

Sources & evidence

ORD record: ord-e984a76f13e44165bf342cd7ca5cbdfb
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673952B2

Reaction notes

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