Hydrochloride methanol → HCID 67958029, compound

HRID 1529356Notes

Reaction equation

C(OC([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[CH:28]=4)[N:23](C(OC(C)(C)C)=O)[CH:22]=3)[CH:18]=[N:17][CH:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.CO.Cl>>[N+:30]([C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[C:19]1[N:20]=[C:15]([N:12]2[CH2:11][CH2:10][CH:9]([NH2:8])[CH2:14][CH2:13]2)[CH:16]=[N:17][CH:18]=1)([O-:32])=[O:31]

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 67959775HCID 67959775, compound

Product 1

HCID 67958029HCID 67958029, compoundYield 23.1%

Conditions

Temperature: 60 °C

Procedure

To tert-butyl 3-(6-(4-(tert-butoxycarbonylamino)piperidin-1-yl)pyrazin-2-yl)-5-nitro-1H-indole-1-carboxylate (170 mg, 0.32 mmol) was added 3N MeOH—HCl (3.5 mL) and then heated at 60° C. overnight. The reaction mixture was quenched with water and neutralized with K2CO3. The resulting precipitate was filtered, washed with water and dried to obtain the crude compound. This crude compound was re-crystallized in ethanol to obtain the title compound as a pale yellow solid (25 mg). MS (ESI, pos. ion) m/z: 339.1 (M+1).

Workup

customThe reaction mixture was quenched with water and neutralized with K2CO3
filtrationThe resulting precipitate was filtered
washwashed with water
customdried
customto obtain the crude compound
customThis crude compound was re-crystallized in ethanol

Sources & evidence

ORD record: ord-3cd7b9fad8c642d2887f668837b26042
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090593B2

Reaction notes

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