Formic Acid → HCID 89622558, compound

HRID 1500810Notes

Reaction equation

HRID 1500810 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.Cl.Cl.Cl.[NH2:14][C:15]1[C:20]2=[C:21]([C:39]3[S:40][C:41]4[C:47]([O:48][CH3:49])=[CH:46][C:45]([CH3:50])=[CH:44][C:42]=4[CH:43]=3)[C:22]([CH2:31][N:32]3[CH2:37][CH2:36][NH:35][C:34](=[O:38])[CH2:33]3)=[C:23]([CH2:24][N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[N:19]2[N:18]=[CH:17][N:16]=1>ClCCl.N1C=CC=CC=1.CO>[NH2:14][C:15]1[C:20]2=[C:21]([C:39]3[S:40][C:41]4[C:47]([O:48][CH3:49])=[CH:46][C:45]([CH3:50])=[CH:44][C:42]=4[CH:43]=3)[C:22]([CH2:31][N:32]3[CH2:37][CH2:36][NH:35][C:34](=[O:38])[CH2:33]3)=[C:23]([CH2:24][N:25]3[CH2:26][CH2:27][N:28]([CH:1]=[O:3])[CH2:29][CH2:30]3)[N:19]2[N:18]=[CH:17][N:16]=1

Participants

7

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 131734278HCID 131734278, compound

Product 1

HCID 89622558HCID 89622558, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic acid anhydride (498 μl, 5.17 mmol) and formic acid (237 μl, 6.28 mmol) were stirred first 2 h at 50° C. and then overnight at rt. Subsequently, the mixture was diluted with dichloromethane (5.1 ml), and 1.16 ml of this solution were added to a solution of Example 49 (233 mg, 370 μmol) in pyridine (89 μl). After stirring at rt for 2 h, the mixture was diluted with methanol and then evaporated. The residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid) affording 77 mg (35% of th.) of title compound.

Workup

  1. customovernight
  2. customat rt
  3. customevaporated
  4. customThe residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid)

Sources & evidence

ORD record
ord-81edb12446fd4ba797feeaeaece4e325
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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