HCID 11111754, compound → HCID 10984079, compound

HRID 1793122Notes

Reaction equation

HRID 1793122 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12](I)[NH:13][C:14]=2[CH2:15][CH2:16][CH3:17])=[O:9])=[CH:4][CH:3]=1>CO>[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]([C:12]3[NH:13][C:14]([CH2:15][CH2:16][CH3:17])=[C:10]([C:8]([NH:7][CH2:6][C:5]4[CH:19]=[CH:20][C:2]([CH3:1])=[CH:3][CH:4]=4)=[O:9])[N:11]=3)[NH:13][C:14]=2[CH2:15][CH2:16][CH3:17])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 11111754HCID 11111754, compound

Product 1

HCID 10984079HCID 10984079, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodide 6c (0.45 g; 1.2 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 triturated with CH3CN. The solid that remained undissolved was collected by filtration and washed with CH3CN to afford 0.30 g (38%) of 1c as an off-white microcrystalline solid. An analytical sample was recrystallized from CH3OH. mp 226–227 C; TLC (CH2Cl2-EtOAc, 1:1): Rf=0.60; 1H NMR (CD2Cl2): δ 0.80 (t, 6H), 1.59 (m, 4H), 2.21 (s, 6H), 2.86 (t, 4H), 4.39 (d, 4H), 7.05 (dd, 8H), 7.22 (br t, 2H); 13C NMR (DMSO-d6): δ 14.2, 21.4, 23.3, 27.0, 49.6, 128.3, 129.9, 131.0, 137.0, 138.7, 164.2; UV/vis (CH3OH): max (M−1cm−1)=287 (25100), 295 (25100), 310 (13700); LRMS (CI+): m/z (%): 513 (100) [M+H]+; HRMS (CI+): calcd for C30H37N6O2 513.2978; found 513.2981; Anal. calcd for C30H36N6O20.33(H2O): C, 68.68; H, 7.17; N, 16.02; found: C, 68.58; H, 7.17; N, 16,11.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated under vacuum
  3. customthe residue was triturated with CH3CN
  4. filtrationThe solid that remained undissolved was collected by filtration
  5. washwashed with CH3CN

Sources & evidence

ORD record
ord-3c49c3434b894b6baf6695c4233a0826
Source dataset
uspto-grants-2006_07
Patent number
US07078528B2

Reaction notes

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