Hydrochloric Acid → HCID 178479015, compound

HRID 2064436Notes

Reaction equation

HRID 2064436 reaction equation
[OH:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:9]([C:15]4[CH:20]=[CH:19][C:18]([C:21]5([NH:25]C(=O)OC(C)(C)C)[CH2:24][CH2:23][CH2:22]5)=[CH:17][CH:16]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1.[ClH:39].CCOC(C)=O>CO.C(Cl)Cl>[ClH:39].[NH2:25][C:21]1([C:18]2[CH:17]=[CH:16][C:15]([C:9]3[C:8]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:7][C:6]4[C:5]5=[N:4][N:3]=[C:2]([OH:1])[N:14]5[CH:13]=[CH:12][C:11]=4[N:10]=3)=[CH:20][CH:19]=2)[CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178452597HCID 178452597, compound

Product 1

HCID 178479015HCID 178479015, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {1-[4-(3-hydroxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate (1-6a) (1.14 g, 2.25 mmol) in MeOH (5 mL) and DCM (15 mL) was added a 4N solution of HCl in EtOAc (22 mL, 88 mmol) at room temperature. After 4 hours the reaction mixture was concentrated in vacuo to give 8-[4-(1-aminocyclobutyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-ol hydrochloride (1-16) as a yellow solid. HRMS (M+H)+: observed=408.1803, calculated=408.1819.

Workup

  1. concentrationAfter 4 hours the reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-a4c9fafb17dc4ed6a010550c12982dcc
Source dataset
uspto-grants-2012_10
Patent number
US08288407B2

Reaction notes

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