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

HRID 1453402Notes

Reaction equation

HRID 1453402 reaction equation
[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:21])=O)=[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(N2C=NC=C2)=O)C=1.CNC(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]([NH2:24])=[O:21])=[CH:17][C:18]=4[N:9]3[CH:8]=[CH:7][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 668140775H-indolo[2,1-a][2]benzazepine-10-carboxamide

Procedure

(5H-indolo[2,1-a][2]benzazepine-10-carboxamide, 13-cyclohexyl-N-[(dimethylamino)sulfonyl]-6,7-dihydro-3-methoxy-6-[methyl[(tetrahydro-2H-pyran-4-yl)carbonyl]amino]-) was prepared from (5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-6,7-dihydro-3-methoxy-6-[methyl[(tetrahydro-2H-pyran-4-yl)carbonyl]amino]-) 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=1.958 min.

Workup

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

Sources & evidence

ORD record
ord-457d96d0486241a1a2e3ab2456df8b68
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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