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Hydrochloride methanol → HCID 67958029, compound

HRID 1529356
Notes
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Reaction equation

HRID 1529356 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 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

  1. customThe reaction mixture was quenched with water and neutralized with K2CO3
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customto obtain the crude compound
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes