Dichloromethane → HCID 90411113, compound

HRID 1754625Notes

Reaction equation

HRID 1754625 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:10]([O:27][C@H:28]1[CH2:32][CH2:31][C@H:30]([N:33]2[CH:41]=[N:40][C:39]3[C:34]2=[N:35][CH:36]=[N:37][C:38]=3[NH2:42])[C@@H:29]1[CH2:43][O:44][C:45]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N.CO.ClCCl>N1C=CC=CC=1>[Si:10]([O:27][C@H:28]1[CH2:32][CH2:31][C@H:30]([N:33]2[CH:41]=[N:40][C:39]3[C:34]2=[N:35][CH:36]=[N:37][C:38]=3[NH:42][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@@H:29]1[CH2:43][O:44][C:45]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:23]([CH3:26])([CH3:24])[CH3:25])([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 21705897Ammonia methanolHCID 90412070HCID 90412070, compound

Product 1

HCID 90411113HCID 90411113, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoyl chloride (0.28 g, 0.231 ml, 2.0 mmol) was added dropwise to a cooled (ice-water bath) solution of compound 61 (0.97 g, 1.33 mmol) in anhydrous pyridine (10 ml). The bath was removed and reaction was stirred overnight, then cooled (ice-water bath) and treated with 2.5 ml of 7 N NH3/MeOH (added over 5 min). The reaction was removed from the bath, stirred under argon for 3 h to decompose the bis-benzoylated by-product and then concentrated in vacuo. The resultant residue was diluted with EtOAc and washed with 10% citric acid, saturated NaHCO3, saturated NaCl, dried over MgSO4 and concentrated in vacuo. The obtained material was chromatographed on silica eluting with 1:1 ethyl acetate: dichloromethane to give N-benzamide 62 (0.98 g, 88% yield) as a white sold foam.

Workup

  1. customThe bath was removed
  2. customreaction
  3. customThe reaction was removed from the bath
  4. stirringstirred under argon for 3 h
  5. concentrationconcentrated in vacuo
  6. additionThe resultant residue was diluted with EtOAc
  7. washwashed with 10% citric acid, saturated NaHCO3, saturated NaCl
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe obtained material was chromatographed on silica eluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-5a55e20d20f14f7c8e1ad545012bd11c
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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