Triethylamine → HCID 22405086, compound

HRID 441254Notes

Reaction equation

HRID 441254 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][C:12](=[O:26])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25])[C:5]([OH:7])=O.P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[CH2:44]([O:46][C:47]([CH2:49][N:50]1[C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=2[NH:54][CH2:53][CH2:52][C:51]1=[O:61])=[O:48])[CH3:45].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][C:12](=[O:26])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25])[C:5]([N:54]1[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=2[N:50]([CH2:49][C:47]([O:46][CH2:44][CH3:45])=[O:48])[C:51](=[O:61])[CH2:52][CH2:53]1)=[O:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 75654Diphenyl chlorophosphateHCID 10848153HCID 10848153, compoundHCID 22405058HCID 22405058, compound

Product 1

HCID 22405086HCID 22405086, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-4-[2-(2-methylphenyl)benzoylamino]benzoic acid (309 mg), diphenyl chlorophosphate (251 mg), 1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (210 mg) in tetrahydrofuran (15 ml) was added triethylamine (172 mg) at 0° C. The resulting mixture was allowed to warm to ambient temperature where it was maintained for 5 hours. The solvent was evaporated and diluted with ethyl acetate and washed with water, diluted hydrochloric acid, saturated sodium bicarbonate aqueous solution and brine. The organic layer was dried over magnesium sulfate and concentrated to give 5-{3-chloro-4-[2-(2-methylphenyl)benzoylamino]benzoyl}-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (390 mg) which was purified by recrystallization from a mixture of ethyl acetate and n-hexane.

Workup

  1. temperaturewas maintained for 5 hours
  2. customThe solvent was evaporated
  3. additiondiluted with ethyl acetate
  4. washwashed with water, diluted hydrochloric acid, saturated sodium bicarbonate aqueous solution and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-59de664324284b98ac9b3a643a21c439
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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