Cyclopentylamine → HCID 57993230, compound

HRID 388777Notes

Reaction equation

HRID 388777 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17](O)=[O:18])[CH2:12][CH2:11]1)=[O:7].[CH:29]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[CH:29]1([NH:34][C:17](=[O:18])[CH2:16][N:13]2[CH2:12][CH2:11][CH:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]3[CH:20]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:22]=[C:3]([C:2]([F:27])([F:1])[F:28])[CH:4]=3)[CH2:15][CH2:14]2)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 2906CyclopentylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57993681HCID 57993681, compound

Product 1

HCID 57993230HCID 57993230, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 2-(4-((3,5-bis(trifluoromethyl)benzamido)methyl)piperidin-1-yl)acetic acid (73 mg, 0.18 mmol), TEA (123 μL, 0.88 mmol), and cyclopentylamine (30 mg, 0.35 mmol) in DMF (1 mL) was treated with a solution of HATU (100 mg, 0.26 mmol) in DMF (1 mL). The reaction mixture was stirred overnight then transferred to a test tube containing saturated aqueous NaHCO3 (4 mL) and EtOAc (4 mL). The biphasic mixture was mixed vigourously and allowed to separate for 15 min. After separation, the mixture was cooled to −20° C. until the aqueous layer was frozen. The organic layer was then poured off and the solvent was removed under reduced pressure at 50° C. The resulting residue was purified by HiTOPs.

Workup

  1. customthen transferred to a test tube
  2. additionThe biphasic mixture was mixed vigourously
  3. customto separate for 15 min
  4. customAfter separation
  5. temperaturewas frozen
  6. additionThe organic layer was then poured off
  7. customthe solvent was removed under reduced pressure at 50° C
  8. customThe resulting residue was purified by HiTOPs

Sources & evidence

ORD record
ord-64e24c0eb3a7481ebc088b41ab563c95
Source dataset
uspto-grants-2013_02
Patent number
US08377968B2

Reaction notes

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