HCID 57796862, compound → HCID 57796807, compound

HRID 1362583Notes

Reaction equation

HRID 1362583 reaction equation
C([O:8][NH:9][C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C@@H:20]([NH:31][C:32]([C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=1)=[O:33])[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)=[O:19])=[O:11])C1C=CC=CC=1>C(#N)C>[OH:8][NH:9][C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C@@H:20]([NH:31][C:32]([C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=1)=[O:33])[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)=[O:19])=[O:11]

Participants

3

Reactant 1

HCID 57796862HCID 57796862, compound

Product 1

HCID 57796807HCID 57796807, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using an analogous method (J15F), the title compound was prepared from naphthalene-2-carboxylic acid[1-(5-benzyloxycarbamoyl-pentylcarbamoyl)-2-(1H-indol-3-yl)-ethyl]-amide (19/98). Yield 7%, foam. 1H NMR (DMSO-d6, HMDSO), δ: 1.10-1.60 (m, 6H); 1.93 (t, 2H, J=7.4 Hz); 2.95-3.30 (m, 4H); 4.65-4.83 (m, 1H); 6.92-7.10 (m, 2H); 7.23 (s, 1H); 7.30 (d, 1H, J=7.6 Hz); 7.53-7.66 (m, 2H); 7.71 (d, 1H, J=7.0 Hz); 7.84-8.04 (m, 4H); 8.09 (br t, 1H, J=5.2 Hz); 8.42 (s, 1H); 8.60 (d, 1H, J=8.2 Hz); 8.68 (br s, 1H); 10.34 (s, 1H); 10.77 (s, 1H). HPLC analysis on Symmetry C8 column: impurities 2.5% (column size 3.9×150 mm; mobile phase acetonitrile −0.1M phosphate buffer (pH 2.5), 40:60; detector UV 220 nm; sample concentration 0.25 mg/ml, flow rate 1.5 ml/min). Anal. Calcd for C28H30N4O4*H2O: C, 66.65; H, 6.39; N, 11.10. Found: C, 66.69; H, 6.00; N, 11.01.

Sources & evidence

ORD record
ord-16804624106242e999e8c2e268a48ee7
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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