HCID 68467898, compound → HCID 24824699, compound

HRID 1927720Notes

Reaction equation

HRID 1927720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][C:41]=1[Cl:42])[C:5]([NH:7][C:8]1[CH:38]=[CH:37][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[CH:15][C:14]=2[CH2:27][NH:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=2)=[CH:10][CH:9]=1)=[O:6]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][C:41]=1[Cl:42])[C:5]([NH:7][C:8]1[CH:38]=[CH:37][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][C:14]=2[CH2:27][NH:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=2)=[CH:10][CH:9]=1)=[O:6]

Participants

3

Reactant 1

HCID 68467898HCID 68467898, compound

Product 1

HCID 24824699HCID 24824699, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

The product of step D (44 mg, 0.073 mmol) was diluted with methylene chloride:TFA (1:1) and stirred for 3 hours. The reaction mixture was concentrated, taken up in ether and sonicated. The solid was filtered, rinsed with ether and dried under vacuum to yield the title compound (35 mg, 88% yield) as white solid. 1H NMR (400 MHz, CDCl3/CD3OD) 8.75 (m, 1H), 8.65 (m, 1H), 8.15 (m, 1H), 8.10 (m, 1H), 8.0 (m, 1H), 7.60 (m, 3H), 7.45 (m, 1H), 7.20 (m, 1H), 6.95 (d, 2H), 6.90 (d, 1H), 4.65 (m, 2H), 3.62 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customsonicated
  3. filtrationThe solid was filtered
  4. washrinsed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ee39216ab9214e3799eb5c4f12f72f94
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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