Diisopropylethylamine → HCID 89907516, compound

HRID 629064Notes

Reaction equation

HRID 629064 reaction equation
CCN(C(C)C)C(C)C.[I:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:14]([OH:16])=O.CN(C(ON1N=NC2C=CC(Cl)=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:46][C:47]([F:57])([F:56])[O:48][C:49]1[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=1>C1COCC1.CN1C(=O)CCC1>[I:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:14]([NH:53][C:52]1[CH:54]=[CH:55][C:49]([O:48][C:47]([F:46])([F:56])[F:57])=[CH:50][CH:51]=1)=[O:16]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6008484-(Trifluoromethoxy)anilineHCID 6216403-Iodo-4-methylbenzoic acidHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate

Product 1

HCID 89907516HCID 89907516, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

DIPEA (4.00 mL, 22.90 mmol) was added to a solution of 3-iodo-4-methylbenzoic acid (2 g, 7.63 mmol) and 2-(6-chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU, 3.47 g, 8.40 mmol) in THF (18 mL) and NMP (2 mL) and the RM was stirred at RT for 30 min. 4-(Trifluoromethoxy)aniline (1.536 mL, 11.45 mmol) was then added and the RM was stirred at RT for 14 h. The solvent was evaporated off under reduced pressure and the residue was treated with aq. 1M HCl (50 mL) and extracted with TBME. The combined extracts were washed with aq. 1 M HCl (50 mL), aq. sat. Na2CO3, water, brine, dried over MgSO4 and the solvent was evaporated off under reduced pressure to give a residue which was crystallized from n-heptane/EtOAc to afford the title compound as white needles. UPLC-MS (Condition 1) tR=3.42 min, m/z=421.9-422.9 [M+H]+, m/z=419.9-420.9 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.44 (s, 3H) 7.36 (d, J=8.3 Hz, 2H) 7.49 (d, J=8.3 Hz, 1H) 7.83-7.93 (m, 3H) 8.39 (d, J=2.0 Hz, 1H) 10.42 (s, 1H).

Workup

  1. stirringthe RM was stirred at RT for 14 h
  2. customThe solvent was evaporated off under reduced pressure
  3. additionthe residue was treated with aq. 1M HCl (50 mL)
  4. extractionextracted with TBME
  5. washThe combined extracts were washed with aq. 1 M HCl (50 mL), aq. sat. Na2CO3, water, brine
  6. dry with materialdried over MgSO4
  7. customthe solvent was evaporated off under reduced pressure
  8. customto give a residue which
  9. customwas crystallized from n-heptane/EtOAc

Sources & evidence

ORD record
ord-1cf9a4f3bcc141c282d4bc492cbf687a
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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