Dichloromethane → HCID 60198721, compound

HRID 2279548Notes

Reaction equation

HRID 2279548 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:12]([NH:23][C:24]([N:26]2[CH2:35][CH2:34][C:33]3[CH:32]=[N:31][C:30]([NH:36][C@@H:37]([CH3:40])[CH2:38][OH:39])=[N:29][C:28]=3[CH2:27]2)=[O:25])[CH2:13][N:14](C)[C:15](=O)OC(C)(C)C)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C(O)(C(F)(F)F)=O.C(Cl)[Cl:49]>>[ClH:49].[F:1][C:2]1[CH:3]=[C:4]([C@H:12]([NH:23][C:24]([N:26]2[CH2:35][CH2:34][C:33]3[CH:32]=[N:31][C:30]([NH:36][C@@H:37]([CH3:40])[CH2:38][OH:39])=[N:29][C:28]=3[CH2:27]2)=[O:25])[CH2:13][NH:14][CH3:15])[CH:5]=[CH:6][C:7]=1[C:8]([F:10])([F:11])[F:9]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86705534HCID 86705534, compound

Product 1

HCID 60198721HCID 60198721, compound

Procedure

To a solution of 318 (0.100 g, 0.175 mmol) and DCM (5 mL) at RT was added TFA (2 mL) and the reaction was stirred at RT for 1 h then concentrated to dryness. The crude product was next dissolved in minimal DCM (with MeOH to aid solubility) and added to a stirred solution of 1M HCl in ether. The resulting solid was filtered, washed with ether and dried to afford 0.070 g (78.8%) of I-80: MS m/z (APCI-pos) M+1=471.

Workup

  1. concentrationthen concentrated to dryness
  2. dissolutionThe crude product was next dissolved in minimal DCM (with MeOH to aid solubility)
  3. additionadded to a stirred solution of 1M HCl in ether
  4. filtrationThe resulting solid was filtered
  5. washwashed with ether
  6. customdried
  7. customto afford 0.070 g (78.8%) of I-80: MS m/z (APCI-pos) M+1=471

Sources & evidence

ORD record
ord-8cfc949c03544c0c8ae993531ddb0822
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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