Diisopropylethylamine → HCID 59536296, compound

HRID 445353Notes

Reaction equation

HRID 445353 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[F:30][C:31]1([F:40])[CH2:36][CH2:35][CH:34]([C:37](O)=[O:38])[CH2:33][CH2:32]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:30][C:31]1([F:40])[CH2:36][CH2:35][CH:34]([C:37]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:9]2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=2)=[O:38])[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27791364,4-Difluorocyclohexanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536296HCID 59536296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.205 g, 0.74 mmol), DIEA (0.14 mL, 0.81 mmol), and 4,4-difluoro-cyclohexanecarboxylic acid (0.13 g, 0.81 mmol) in DMF (4 mL) was added HATU (0.31 g, 0.81 mmol). The reaction mixture was continued to stir for 2 h, quenched with H2O, and extracted with DCM (3×). The organic extracts were dried over Na2SO4, concentrated and purified by ISCO (20% EtOAc/hexanes) to give the white solid. MS (ESI, positive ion) m/z: 424 (M+1).

Workup

  1. customquenched with H2O
  2. extractionextracted with DCM (3×)
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by ISCO (20% EtOAc/hexanes)
  6. customto give the white solid

Sources & evidence

ORD record
ord-b35ace90e18c4edb9b1145d0e426128b
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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