Trifluoroacetic acid → 5H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide

HRID 1453404Notes

Reaction equation

HRID 1453404 reaction equation
[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19](O)=[O:20])=[CH:17][C:18]=4[N:9]3[CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C1N=C[N:24]([C:27](N2C=NC=C2)=[O:28])C=1.C[NH:35]C(N)=O.C(O)(C(F)(F)F)=O>>[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([NH2:35])=[O:20])=[CH:17][C:18]=4[N:9]3[CH:8]=[C:7]([C:27]([NH2:24])=[O:28])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 11719MethylureaHCID 682631,1'-CarbonyldiimidazoleHCID 685639665H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

Product 1

HCID 688492915H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide

Procedure

(5H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N˜10˜-[(dimethylamino)sulfonyl]-6,7-dihydro-3-methoxy-N˜6˜-methyl-N˜6˜-[(tetrahydro-2-furanyl)methyl]-) was prepared from (5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-6,7-dihydro-3-methoxy-6-[[methyl[(tetrahydro-2-furanyl)methyl]amino]carbonyl]-) using CDI as a coupling reagent in a similar manner as described before; Analytical HPLC method: Solvent A=10% MeO{tilde over (H)}90% H2Õ0.1% TFA, Solvent B=90% MeO{tilde over (H)}10% H2O0.1% 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)+=637.27, HPLC Rt=1.953 min.

Workup

  1. customB=100, Gradient time=2 min, Flow Rate=5 ml/min, Column

Sources & evidence

ORD record
ord-90eab9f371e849a9b1e10a4192b10721
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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