Tetrahydrofuran → HCID 178425720, compound

HRID 1629761Notes

Reaction equation

HRID 1629761 reaction equation
[NH2:1][C@@:2]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[CH:19][CH:18]=1)([C:13]([F:16])([F:15])[F:14])[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[O:5].C1CCC(N=C=NC2CCCCC2)CC1.[N:46]1[N:47](CC(O)=O)[N:48]=[N:49][CH:50]=1.C1C[O:58][CH2:57][CH2:56]1>>[NH:46]1[C:50]([CH2:56][C:57]([NH:1][C:2]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27]([F:28])([F:29])[F:30])=[CH:19][CH:18]=2)([CH2:3][C:4](=[O:5])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[C:13]([F:16])([F:15])[F:14])=[O:58])=[N:49][N:48]=[N:47]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 10868DicyclohexylcarbodiimideHCID 890302H-Tetrazol-2-acetic acidHCID 86685849(S)-3-Amino-4,4,4-trifluoro-1-p-tolyl-3-(4-(4,4,4-trifluorobutoxy)phenyl)-butan-1-one

Product 1

HCID 178425720HCID 178425720, compoundYield 152%

Conditions

Temperature
0 °C

Procedure

To a solution of Intermediate 2F (789 mg, 1.82 mmol) in anhydrous THF (9 ml) at 0° C. was added DCC (1.13 g, 5.46 mmol). 2-Tetrazole acetic acid (700 mg, 5.46 mmol) was added dropwise as a suspension in anhydrous THF (8 mL). The reaction was stirred at 0° C. for 1 h and then at rt overnight. The reaction was filtered and solids were rinsed with THF. The filtrate was diluted with EtOAc (40 mL), washed with sat'd Na2CO3 and sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated to provide Intermediate 2G (1.5 g, 152%) as a reddish brown solid. Intermediate 2G. was used in the next step without further purification. LCMS Anal. Calc'd for C24H23F6N5O3 543.46, found [M+H] 543.9.

Workup

  1. customat rt
  2. customovernight
  3. filtrationThe reaction was filtered
  4. washsolids were rinsed with THF
  5. additionThe filtrate was diluted with EtOAc (40 mL)
  6. washwashed with sat'd Na2CO3
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ee86fc6a067d4bb5af4ffcb248898c30
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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