Hydrochloric Acid → HCID 178466657, compound

HRID 225998Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]2[C:21]([CH3:22])=[C:20]([N:23]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C:24]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[CH:28][CH:27]=3)=[O:25])[N:19]3[N:40]=[CH:41][C:42]([C:43]([O:45]CC)=[O:44])=[C:18]3[N:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CC(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([NH:15][C:16]2[C:21]([CH3:22])=[C:20]([N:23]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])[C:24]([C:26]3[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH3:34])=[CH:30][CH:31]=3)=[O:25])[N:19]3[N:40]=[CH:41][C:42]([C:43]([OH:45])=[O:44])=[C:18]3[N:17]=2)[CH2:13][CH2:14]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred suspension of ethyl 5-({trans-4-[(tert-butoxy)carbonylamino]cyclohexyl}amino)-7-[(tert-butoxy)-N-(4-ethoxyphenyl)carbonylamino]-6-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate (5.55 g) in 2-propanol (136 mL) was added 2 mol/L aqueous NaOH (34 mL). The resulting mixture was stirred at 50° C. for 40 h, and then at 80° C. for 4 h. The mixture was acidified (pH 4) with 1 mol/L aqueous HCl and concentrated in vacuo. The residue was suspended in water (150 mL) and slowly stirred for 1 h. The precipitate was filtered and dried in vacuo to give the title compound (5.35 g, yield 78%) as a white solid. The 1H-NMR and ESI/MS data for this compound are shown below.

Workup

waitat 80° C. for 4 h
concentrationconcentrated in vacuo
stirringslowly stirred for 1 h
filtrationThe precipitate was filtered
customdried in vacuo

Sources & evidence

ORD record: ord-715f42d75bdd47e78a636aa6851d4181
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557110B2

Reaction notes

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