Triethylamine → HCID 57526554, compound

HRID 1982891Notes

Reaction equation

HRID 1982891 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:30]([NH:32][S:33]([N:36]([CH3:38])[CH3:37])(=[O:35])=[O:34])=[O:31])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([C:21](O)=[O:22])[CH2:18][C:17]4[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.C1(P([N:60]=[N+:61]=[N-:62])(C2C=CC=CC=2)=O)C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:30]([NH:32][S:33]([N:36]([CH3:37])[CH3:38])(=[O:34])=[O:35])=[O:31])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([C:21]([N:60]=[N+:61]=[N-:62])=[O:22])[CH2:18][C:17]4[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59682116HCID 59682116, compound

Product 1

HCID 57526554HCID 57526554, compound

Reagents, catalysts & solvents 1

HCID 21877217Toluene methylene chlorideSolvent

Procedure

To a mixture of the acid, 13-cyclohexyl-10-((((dimethylamino)sulfonyl)amino)carbonyl)-3-(methyloxy)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6-carboxylic acid, (427.2 mg, 0.79 mmol) in a mixture of PhMe/CH2Cl2 (6 ml/2 ml) at r.t. under N2 was added triethylamine (117 mg, 1.16 mmol), followed by diphenylphosphoryl azide (DPPA) (320 mg, 1.16 mmol). The mixture was stirred at r.t. for 4 hr. The volatiles were then evaporated. The residue was titurated with hydrochloric acid (3× 10 ml, 1N), dried and the crude azide, 13-cyclohexyl-10-((((dimethylamino)sulfonyl)amino)carbonyl)-3-(methyloxy)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6-carbonyl azide, was used without further purification Analytical HPLC method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Flow Rate=5 ml/min, Column: Xterra MS C18 S7 3.0×50 mm; LC/MS: (ES+) m/z (M+H)+=565.21, HPLC Rt=1.988 min.

Workup

  1. customThe volatiles were then evaporated
  2. customdried
  3. customthe crude azide, 13-cyclohexyl-10-((((dimethylamino)sulfonyl)amino)carbonyl)-3-(methyloxy)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6-carbonyl azide, was used without further purification Analytical HPLC method
  4. customB=100, Gradient time=2 min, Flow Rate=5 ml/min, Column

Sources & evidence

ORD record
ord-5809a88d078c44df81d93e5a5e408105
Source dataset
uspto-grants-2009_06
Patent number
US07541352B2

Reaction notes

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