2-Iodobenzoic acid → HCID 71768544, compound

HRID 1746909Notes

Reaction equation

HRID 1746909 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:12]=[CH:11][N:10]([C:13]3[N:34]=[CH:33][CH:32]=[CH:31][C:14]=3[C:15]([NH:17][CH:18]([CH:26]([OH:30])[C:27]([NH2:29])=[O:28])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:16])[N:9]=2)[C:3]2[CH:35]=[CH:36][CH:37]=[CH:38][C:2]1=2.IC1C=CC=CC=1C(O)=O>CS(C)=O>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:12]=[CH:11][N:10]([C:13]3[N:34]=[CH:33][CH:32]=[CH:31][C:14]=3[C:15]([NH:17][CH:18]([C:26](=[O:30])[C:27]([NH2:29])=[O:28])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:16])[N:9]=2)[C:3]2[CH:35]=[CH:36][CH:37]=[CH:38][C:2]1=2

Participants

4

Reactant 2

HCID 69412-Iodobenzoic acidHCID 89852017HCID 89852017, compound

Product 1

HCID 71768544HCID 71768544, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Oxidation of 2-(3-((2H-benzo[b][1,4]oxazin-4(3H)-yl)methyl)-1H-pyrazol-1-yl)-N-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)nicotinamide (210 mg, 0.410 mmol) in DMSO (6 mL) with 2-iodobenzoic acid as described for example 2.4 gave 220 mg of a yellow solid, which was purified by chromatography over silica gel (eluent CH2Cl2+0-15% methanol). After concentration the obtained solid was recrystallized from 2-propanol to give 78 mg of the title compound as an amorphous solid; ESI-MS [M+H]+: 511.2. 1H-NMR (400 MHz, DMSO), δ[ppm]: 8.97 (m, 1H), 8.55 (m, 1H), 8.29 (m, 1H), 8.09 (m, 1H), 7.84 (m, 1H), 7.70 (m, 1H), 7.44 (m, 1H), 7.31 (m, 4H), 7.22 (m, 1H), 6.82 (m, 1H), 6.70 (m, 1H), 6.61 (m, 1H), 6.50 (m, 1H), 6.34 (m, 1H), 5.44 (m, 1H), 4.26 (d, 1H), 4.20 (d, 1H), 4.12 (m, 2H), 3.25 (m, 3H), 2.88 (dd, 1H).

Sources & evidence

ORD record
ord-1f8bb488d3e747a28f0c5ed00a45b748
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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