Triethylamine → HCID 69871576, compound

HRID 2084991Notes

Reaction equation

HRID 2084991 reaction equation
C(N(CC)CC)C.O[C:9]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:21](=[O:35])[NH:22][C:23](=[O:34])[C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=2)=[CH:15][CH:14]=1)=[O:10].Cl.[NH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][NH:44][C:45](=[O:47])[CH3:46].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(N(CC)C=O)C.C(OCC)(=O)C>[C:45]([NH:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][NH:37][C:9]([CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20]2[C:21](=[O:35])[NH:22][C:23](=[O:34])[C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=2)=[CH:17][CH:18]=1)=[O:10])(=[O:47])[CH3:46]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13030900HCID 13030900, compoundHCID 22728596HCID 22728596, compound

Product 1

HCID 69871576HCID 69871576, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 12051DiethylformamideSolvent

Procedure

A solution of triethylamine (81 mg, 0.8 mmol) in dry N,N-diethylformamide (5 mL) was added to a mixture of 3-[4-[2-(hydroxycarbonyl)ethyl]phenylamino]-4-(3-nitrophenyl)-1H-pyrrole-2,5-dione (Example A763, 152 mg, 0.4 mmol), N-(6-aminohexyl)acetamide hydrochloride (78 mg, 0.4 mmol), 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (77 mg, 0.4 mmol) and 1-hydroxybenzotriazole (54 mg, 0.4 mmol) and the resulting mixture stirred at room temperature for 18 hours. The mixture was diluted with ethyl acetate (25 mL) and washed successively with water (2×25 mL), saturated aqueous sodium bicarbonate solution (25 mL), water (2×25 mL), brine (25 mL), dried over magnesium sulphate and concentrated. The residue was redissolved in dichloromethane-methanol (1:1 v/v), filtered and evaporated to afford the title compound as a foam.

Workup

  1. washwashed successively with water (2×25 mL), saturated aqueous sodium bicarbonate solution (25 mL), water (2×25 mL), brine (25 mL)
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated
  4. dissolutionThe residue was redissolved in dichloromethane-methanol (1:1 v/v)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-84bf6c7487244107b05592ed24f7cb8b
Source dataset
uspto-grants-2004_04
Patent number
US06719520B2

Reaction notes

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