Guanidine Hydrochloride → 8-Amino-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester

HRID 222127Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=O)[C:9]=2[N:8]([CH3:16])[C:7]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:5])[CH3:2].[C:24](OC(OC(C)(C)C)N(C)C)(C)(C)C.Cl.[NH2:39][C:40]([NH2:42])=[NH:41].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][C:11]3[C:10]([C:9]=2[N:8]([CH3:16])[C:7]=1[C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])=[N:39][C:40]([NH2:42])=[N:41][CH:24]=3)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester XXVIA (4.67 mmol) in DMF (20 mL), N,N-dimethylformamide di -tert-butyl acetal (2 mL) was added and the solution was stirred at 100° C. overnight. After cooling to rt guanidine hydrochloride (14 mmol) and K2CO3 (14 mmol) were added and the mixture was heated at 100° C. for 24 h. The organic solvent was evaporated to dryness. Chromatography on silica gel (AcOEt/hexane 1:1) afforded the title compound (80% yield). ESI (+) MS: m/z 373 (MH+). 1H NMR: 1.28 (t, J=7.07, 3H), 1.55 (s, 9H), 2.68 (t, J=7.80, 2H), 2.79 (t, J=7.80, 2H), 4.18 (s, 3H), 4.23 (q, J=7.07, 2H), 6.40 (bs, 2H), 7.97 (s, 1H).

Workup

additionwere added
temperaturethe mixture was heated at 100° C. for 24 h
customThe organic solvent was evaporated to dryness

Sources & evidence

ORD record: ord-be79162f6d0d48448c0d360c2249c945
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207180B2

Reaction notes

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