Triethylamine → HCID 18917536, compound

HRID 1290972Notes

Reaction equation

HRID 1290972 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)([OH:3])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClN1C(=O)CCC1=O.[Cl:42][C:43]1[CH:64]=[C:63]([NH2:65])[CH:62]=[CH:61][C:44]=1[C:45]([N:47]1[C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=2[CH2:51][N:50]2[CH:58]=[CH:59][CH:60]=[C:49]2[CH2:48]1)=[O:46].C(N(CC)CC)C>ClCCl.O1CCCC1.ClCCl>[Cl:42][C:43]1[CH:64]=[C:63]([NH:65][C:1](=[O:3])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[CH:62]=[CH:61][C:44]=1[C:45]([N:47]1[C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=2[CH2:51][N:50]2[CH:58]=[CH:59][CH:60]=[C:49]2[CH2:48]1)=[O:46]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 7285212-(1H-pyrrol-1-yl)benzoic acidHCID 10806897HCID 10806897, compound

Product 1

HCID 18917536HCID 18917536, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A solution of 1-(2-carboxyphenyl)pyrrole (188 mg, 1 mmol) and triphenylphosphine (264 mg, 1 mmol) in dichloromethane (6 ml) was cooled to 0° C. To this solution was added, portionwise, N-chlorosuccinimide (131 mg, 0.9 mmol). The solution was stirred for 30 minutes and allowed to warm to room temperature. To this solution was added a solution of 10,11-dihydro-10-(2-chloro-4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine (338 mg, 1 mmol) and triethylamine (0.15 ml, 1.06 mmol) in 15 ml of a mixture of a tetrahydrofuran-dichloromethane (1:2). The reaction was stirred for two hours at room temperature and then was concentrated to a solid in vacuo. The solid was disolved in ether (100 ml) and filtered. The filtrate was concentrated in vacuo and chromatographed over silica gel with ethyl acetate-hexane (1:1) as the mobile phase to afford 270 mg of the product as a yellow solid. Recrystallization from ethyl acetate-ether-hexane gave 180 mg of the product as a colorless solid. MS (EI),m/z 506/508 (M+).

Workup

  1. additionTo this solution was added
  2. stirringThe reaction was stirred for two hours at room temperature
  3. concentrationwas concentrated to a solid in vacuo
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customchromatographed over silica gel with ethyl acetate-hexane (1:1) as the mobile phase

Sources & evidence

ORD record
ord-4069c8828c1c4e96ad033c9bc3a2a517
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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