Diisopropylethylamine → HCID 67360421, compound

HRID 1667298Notes

Reaction equation

HRID 1667298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14](O)=[O:15])[C:9]2=[O:17])=[CH:4][CH:3]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[OH:33])=[CH:28][CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:40]2[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=2)([OH:33])[CH:34]2[CH2:35][CH2:36][N:37]([C:14](=[O:15])[CH2:13][N:10]3[CH2:11][CH2:12][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)([C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)[C:9]3=[O:17])[CH2:38][CH2:39]2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 673571912-(3,3-Bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid

Product 1

HCID 67360421HCID 67360421, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the product of Example 58D (171 mg, 0.518 mmol), the product of Example 32A (157 mg, 0.518 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (197 mg, 0.518 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.361 mL, 2.07 mmol) in CH2Cl2 (5 mL) was stirred at ambient temperature for 36 hours. The reaction mixture was diluted by CH2Cl2, and the organic mixture was washed with 1 N aqueous HCl and saturated NaHCO3 solution and brine, dried with Na2SO4, filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix® Intelliflash™ 280; SF15-24 g column; 50% ethyl acetate/hexanes) to afford purified material that was taken up in a minimal amount of ether. Addition of hexanes caused formation of a solid that was collected by vacuum filtration and air-dried to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.59-7.47 (m, 4H), 7.40-7.29 (m, 4H), 7.18-7.04 (m, 8H), 5.48 (s, 1H), 4.41-4.29 (m, 1H), 4.19 (d, J=16.5, 1H), 4.09 (d, J=16.6, 1H), 3.86-3.75 (m, 1H), 3.38-3.30 (m, 2H), 3.05-2.89 (m, 1H), 2.85-2.63 (m, 3H), 2.63-2.51 (m, 1H), 1.40-1.17 (m, 4H); MS (DCI+) m/z 617 (M+H)+.

Workup

  1. washthe organic mixture was washed with 1 N aqueous HCl and saturated NaHCO3 solution and brine
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was chromatographed on silica gel (Analogix® Intelliflash™ 280; SF15-24 g column; 50% ethyl acetate/hexanes)
  6. customto afford
  7. custompurified material that
  8. additionAddition of hexanes caused formation of a solid
  9. filtrationthat was collected by vacuum filtration
  10. customair-dried

Sources & evidence

ORD record
ord-654282dce47c4fa590cf4d8143da5184
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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