Dichloromethane → HCID 60198594, compound

HRID 2279527Notes

Reaction equation

HRID 2279527 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][CH:37]([CH3:39])[CH3:38])=[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:48]>>[ClH:48].[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][CH:37]([CH3:39])[CH3:38])=[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:9])([F:10])[F:11]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68294104HCID 68294104, compound

Product 1

HCID 60198594HCID 60198594, compound

Procedure

To a solution of 268 (0.075 g, 0.14 mmol) and DCM (3 mL) at RT was added TFA (2 mL) and the reaction was stirred at RT for 1 h then concentrated to dryness. The resulting product was next dissolved in minimal DCM (with MeOH to increase solubility) and added with stirring to a solution of 1M HCl in ether. The resulting solid was filtered, washed with ether and dried to afford 0.050 g (75%) of I-66: MS m/z (APCI-pos) M+1=455.

Workup

  1. concentrationthen concentrated to dryness
  2. dissolutionThe resulting product was next dissolved in minimal DCM (with MeOH to increase solubility)
  3. additionadded
  4. stirringwith stirring to a solution of 1M HCl in ether
  5. filtrationThe resulting solid was filtered
  6. washwashed with ether
  7. customdried
  8. customto afford 0.050 g (75%) of I-66

Sources & evidence

ORD record
ord-4dc0afab39a94a658e36020425d2a5d2
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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