HCID 118415282, compound → HCID 118415264, compound

HRID 1775781Notes

Reaction equation

HRID 1775781 reaction equation
C1C2C(C[C@:15]([NH:58][C:59](=[O:64])[C:60]([NH2:63])([CH3:62])[CH3:61])([CH:55]([CH3:57])[CH3:56])[C:16]([N:18]([C@@H:20]([CH:50]3[CH2:54][CH2:53][CH2:52][CH2:51]3)[C@H:21]([O:48][CH3:49])[CH2:22][C:23]([N:25]3[CH2:29][CH2:28][CH2:27][C@H:26]3[C@H:30]([O:46][CH3:47])[C@@H:31]([CH3:45])[C:32]([NH:34][C@H:35]([CH3:44])[C@@H:36]([OH:43])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:33])=[O:24])[CH3:19])=[O:17])C3C(=CC=CC=3)C=2C=CC=1>C(Cl)Cl>[NH2:63][C:60]([CH3:62])([CH3:61])[C:59]([NH:58][C@@H:15]([CH:55]([CH3:57])[CH3:56])[C:16]([N:18]([C@@H:20]([CH:50]1[CH2:51][CH2:52][CH2:53][CH2:54]1)[C@H:21]([O:48][CH3:49])[CH2:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[C@H:30]([O:46][CH3:47])[C@@H:31]([CH3:45])[C:32]([NH:34][C@H:35]([CH3:44])[C@@H:36]([OH:43])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:33])=[O:24])[CH3:19])=[O:17])=[O:64]

Participants

3

Reactant 1

HCID 118415282HCID 118415282, compound

Product 1

HCID 118415264HCID 118415264, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To above product (16) was added DEA (3 mL)/CH2Cl2 (3 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with water and dried over sodium sulphate. After concentrated in vacuo, the residue was purified by flash chromatography on silica-gel (MeOH/CH2Cl2, 1:10) to give the desired product 17 (121.0 mg, 58.4% for two steps). LC-MS: m/z 703.0[M+H]+; 1H NMR (400 MHz, DMSO) δ 8.41 (m, 2H), 7.30-7.11 (m, 5H), 4.80-4.10 (m, 4H), 4.00-3.50 (m, 3H), 3.35-2.65 (m, 14H), 2.44-1.90 (m, 4H), 1.89-1.60 (m, 5H), 1.60 (m, 20H), 1.15-0.70 (m, 6H).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over sodium sulphate
  3. concentrationAfter concentrated in vacuo
  4. customthe residue was purified by flash chromatography on silica-gel (MeOH/CH2Cl2, 1:10)

Sources & evidence

ORD record
ord-c387c5c4ce2742978806da99944e8eea
Source dataset
uspto-grants-2016_02
Patent number
US09260478B2

Reaction notes

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