HCID 11042299, compound → HCID 136365981, compound

HRID 1821890Notes

Reaction equation

HRID 1821890 reaction equation
[C:1]1([C:7]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O:22][C:23](=[O:29])[NH:24][CH2:25][CH2:26][O:27][NH2:28])([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl.CO>[C:1]1([C:7](=[N:28][O:27][CH2:26][CH2:25][NH:24][C:23](=[O:29])[O:22][C:18]([CH3:20])([CH3:19])[CH3:21])[C:9]2[C:17]3[C:12](=[CH:13][N:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11042299HCID 11042299, compoundHCID 15610443tert-butyl N-(2-(aminooxy)ethyl)carbamate

Product 1

HCID 136365981HCID 136365981, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

tert-Butyl 2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-3-yl)methylene]amino]oxy]ethylcarbamate (429.2 mg, 89%) was prepared as a white foam using phenyl(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone (Reference Example 8) and tert-butyl[2-(aminooxy)ethyl]carbamate following the procedure described for Example 104: Rf 0.42 (90:10 methylene chloride/methanol); 1H NMR (300 MHz, CD3OD) δ1.38-1.39 (9H, s), 3.40-3.44 (2H, m), 3.17-3.20 (1H, t, J=5.7 Hz), 3.26-3.28 (1H, t, J=5.3 Hz), 6.50-6.80 (1H, m), 7.30-7.50 (5H, m), 7.86-8.32 (2H, m), 8.76 (1H, s); ESI MS m/z 381 [C21H24N4O3+H]+; HPLC (Method A) 96.8% (AUC), tR=17.7 min.

Sources & evidence

ORD record
ord-16a7c9aa69374ce1899b9d2bb489c76b
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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