1-Pyrrolidineethanamine → HCID 86604203, compound

HRID 1160437Notes

Reaction equation

HRID 1160437 reaction equation
C(O[C:4]([C:6]1[C:7](=[O:25])[C:8]2[CH:22]=[N:21][C:20]([S:23][CH3:24])=[N:19][C:9]=2[N:10]2[C:18]=1[S:17][C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=1)=[O:5])C.[N:26]1(CCN)[CH2:30][CH2:29][CH2:28][CH2:27]1.[Al+3].[Cl-].[Cl-].[Cl-].[C:38]([CH:41]([CH:43](C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(Cl)Cl.[OH-].[Na+]>[CH:28]1([CH2:29][CH2:30][NH:26][C:4]([C:6]2[C:7](=[O:25])[C:8]3[CH:22]=[N:21][C:20]([S:23][CH3:24])=[N:19][C:9]=3[N:10]3[C:18]=2[S:17][C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]3=2)=[O:5])[CH2:27][CH2:43][CH2:41][CH2:38]1

Participants

7

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 6451240Aluminum(III) ChlorideHCID 9855836Potassium sodium tartarateHCID 59516512HCID 59516512, compound

Product 1

HCID 86604203HCID 86604203, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-methylsulfanyl-5-oxo-5H-7-thia-1,3,11b-triaza-benzo[c]fluorene-6-carboxylic acid ethyl ester (230 mg, 0.619 mmol) and 2-(pyrrolidin-1-yl)ethanamine (0.24 mL, 1.854 mmol) in DCM (15 mL) was added solid AlCl3 (250 mg, 1.875 mmol) at rt. The reaction was stirred for 1 h at rt and diluted with DCM (100 mL), conc. sodium potassium tartrate (30 mL), and NaOH (6N, 10 mL). The mixture was stirred for 15 min and the layers were separated. The aqueous layer was extracted with DCM (50 mL) and the combined organic layer was washed with brine (50 mL). The crude reaction mixture was dried over Na2SO4, and concentrated to yield the desired product as a yellow solid (250 mg, 92%). MS (m/z): 440 (MH+). 1H NMR (CDCl3) δ: 10.26 (br, 1H), 9.61 (s, 1H), 9.55 (m, 1H), 7.77 (m, 1H), 7.57 (m, 1H), 7.50 (m, 1H), 3.67 (q, 2H), 2.81 (s, 3H), 2.77 (t, 2H), 2.63 (m, 4H), 1.82 (m, 4H).

Workup

  1. stirringThe mixture was stirred for 15 min
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with DCM (50 mL)
  4. washthe combined organic layer was washed with brine (50 mL)
  5. customThe crude reaction mixture
  6. dry with materialwas dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7e0fb350271f4ba08df121fca87a7510
Source dataset
uspto-grants-2010_10
Patent number
US07816406B2

Reaction notes

Loading…