Formic Acid → HCID 89620522, compound

HRID 1500812Notes

Reaction equation

HRID 1500812 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH2:25][C:26]1[C:31]2=[C:32]([C:47]3[S:48][C:49]4[C:55]([O:56][CH3:57])=[CH:54][C:53]([CH3:58])=[CH:52][C:50]=4[CH:51]=3)[C:33]([CH2:42][NH:43][C:44](=[O:46])[CH3:45])=[C:34]([CH2:35][N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[N:30]2[N:29]=[CH:28][N:27]=1>ClCCl.N1C=CC=CC=1.CO>[NH2:25][C:26]1[C:31]2=[C:32]([C:47]3[S:48][C:49]4[C:55]([O:56][CH3:57])=[CH:54][C:53]([CH3:58])=[CH:52][C:50]=4[CH:51]=3)[C:33]([CH2:42][NH:43][C:44](=[O:46])[CH3:45])=[C:34]([CH2:35][N:36]3[CH2:37][CH2:38][N:39]([CH:1]=[O:3])[CH2:40][CH2:41]3)[N:30]2[N:29]=[CH:28][N:27]=1

Participants

7

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 89622429HCID 89622429, compound

Product 1

HCID 89620522HCID 89620522, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic acid anhydride (304 μl, 3.16 mmol) and formic acid (145 μl, 3.16 mmol) were stirred first 2 h at 50° C. and then overnight at rt. Subsequently, the mixture was diluted with dichloromethane (3.1 ml), and 663 μl of this solution were added to a solution of Example 63 (160 mg, 226 μmol) in pyridine (54 μl). The mixture was stirred at rt for 2 h, then diluted with methanol (1 ml), and stirring was continued at 40° C. for another 2 h. After evaporation, the residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid) affording 74 mg (61% of th.) of title compound.

Workup

  1. customovernight
  2. customat rt
  3. stirringstirring
  4. waitwas continued at 40° C. for another 2 h
  5. customAfter evaporation
  6. customthe residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid)

Sources & evidence

ORD record
ord-5a3b7bacd48d4e03a4917e8b2ae3330a
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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