Formic Acid → HCID 86597716, compound

HRID 547834Notes

Reaction equation

HRID 547834 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[CH2:11]([O:18][CH2:19][C@@H:20]1[CH2:25][NH:24][CH2:23][CH2:22][N:21]1[C:26]1[N:31]=[CH:30][C:29]([N:32]([CH3:52])[C:33](=[O:51])[C:34]([C:37]2[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[C:39]([C:47]([F:50])([F:49])[F:48])[CH:38]=2)([CH3:36])[CH3:35])=[C:28]([C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][C:54]=2[CH3:60])[CH:27]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([O:18][CH2:19][C@@H:20]1[CH2:25][N:24]([CH:1]=[O:3])[CH2:23][CH2:22][N:21]1[C:26]1[N:31]=[CH:30][C:29]([N:32]([CH3:52])[C:33](=[O:51])[C:34]([C:37]2[CH:42]=[C:41]([C:43]([F:44])([F:45])[F:46])[CH:40]=[C:39]([C:47]([F:50])([F:49])[F:48])[CH:38]=2)([CH3:35])[CH3:36])=[C:28]([C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][C:54]=2[CH3:60])[CH:27]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 86597717HCID 86597717, compound

Product 1

HCID 86597716HCID 86597716, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 0.35 ml (3.7 mmol) acetic anhydride and 0.17 ml (4.6 mmol) formic acid was heated at 50° C. for 2 h. After cooling to room temperature a portion of 0.08 ml of this mixture was added to 0.5 ml THF. A solution of 0.10 g (0.14 mmol) (S)-N-[6-(2-benzyloxymethyl-piperazin-1-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide (Example 383a)) in 1 ml THF was added dropwise at 0° C. Conversion was monitored by thin layer chromatography. After complete consumption of the starting material the reaction mixture was diluted with water and extracted with three portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to give 0.11 g of crude (S)-N-[6-(2-benzyloxymethyl-4-formyl-piperazin-1-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide as a light yellow solid.

Workup

  1. customAfter complete consumption of the starting material the reaction mixture
  2. additionwas diluted with water
  3. extractionextracted with three portions of dichloromethane
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf14e963a8404961bdbfe9db9415b06b
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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