HCID 10892946, compound → HCID 11047916, compound

HRID 1793125Notes

Reaction equation

HRID 1793125 reaction equation
I[C:2]1[NH:3][C:4]([CH2:14][CH2:15][CH3:16])=[C:5]([C:7]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])[N:6]=1>CO>[CH2:14]([C:4]1[NH:3][C:2]([C:2]2[NH:3][C:4]([CH2:14][CH2:15][CH3:16])=[C:5]([C:7]([N:9]3[CH2:10][CH2:11][CH2:12][CH2:13]3)=[O:8])[N:6]=2)=[N:6][C:5]=1[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:8])[CH2:15][CH3:16]

Participants

3

Reactant 1

HCID 10892946HCID 10892946, compound

Product 1

HCID 11047916HCID 11047916, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodide 6f (0.34 g; 1.0 mmol) was used as starting material. After cooling to rt, the reaction mixture was diluted with CH3OH and filtered. The filtrate was evaporated under vacuum, and the residue was recrystallized from CH3OH to afford 0.080 g (38%) of 1f as yellow prisms. mp>260 C; TLC (EtOAc): Rf=0.14; 1H NMR (DMSO-d6): δ 0.84 (t, 6H), 1.59 (m, 4H), 1.80 (br m, 8H), 2.80 (t, 4H), 3.55 (br m, 4H), 3.90 (br m, 4H); 13C NMR (DMSO-d6): δ 14.3, 23.4, 24.2, 26.9, 31.4, 46.8, 49.0, 132.9, 138.0, 163.7; UV/vis (CH3OH): max (M31 1cm−1)=287 (21200), 294 (20900), 309 (sh); LRMS (CI+): m/z (%): 208 (100), 413 (70) [M+H]+; HRMS (CI+): calcd for C22H33N6O2 413.2665; found 413.2662; Anal. calcd for C22H32N6O20.33(H2O): C, 63.13; H, 7.87; N, 20.08; found: C, 63.21; H, 7.82; N, 20.08.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated under vacuum
  3. customthe residue was recrystallized from CH3OH

Sources & evidence

ORD record
ord-1471d6ffb8994112af60f9816c4686ad
Source dataset
uspto-grants-2006_07
Patent number
US07078528B2

Reaction notes

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