Water → HCID 178511584, compound

HRID 1257687Notes

Reaction equation

HRID 1257687 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:24]3[C:16](=[CH:17][N:18]=[C:19]4[C:23]=3[CH:22]=[CH:21][NH:20]4)[N:15]=[N:14]2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.O>C(Cl)Cl>[N:13]1([C@H:10]2[CH2:11][CH2:12][C@H:8]([NH2:7])[CH2:9]2)[C:24]2[C:16](=[CH:17][N:18]=[C:19]3[C:23]=2[CH:22]=[CH:21][NH:20]3)[N:15]=[N:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 178453992HCID 178453992, compound

Product 1

HCID 178511584HCID 178511584, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of racemic trans [3-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester (900 mg, 2.63 mmol), trifluoroacetic acid (5 mL), water (50.0 μL) and DCM (10 mL) was stirred at ambient temperature for 5 hours. The solvents were removed in vacuo and the resulting residue purified by column chromatography (SCX-2, gradient: methanol to 2M NH3 in methanol) to give 586 mg (92%) of racemic trans 3-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentylamine as a white foam solid. LCMS (Method B, ESI): RT=0.36 & 1.05 min, m+H=243.3; 1H NMR (400 MHz, DMSO) δ: 12.35 (br s, 1H), 8.98 (s, 1H), 7.59 (d, 1H), 6.98 (d, 1H), 5.67 (m, 1H), 3.67 (m, 1H), 2.52 (m, 1H, partially obscured by DMSO), 2.40 (m, 1H), 2.25-2.03 (m, 3H), 1.54 (m, 1H).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe resulting residue purified by column chromatography (SCX-2, gradient: methanol to 2M NH3 in methanol)

Sources & evidence

ORD record
ord-65955cc80cec4a8a95d77a7d3a7b1756
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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