Diisopropylethylamine → HCID 59451479, compound

HRID 1874981Notes

Reaction equation

HRID 1874981 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][CH2:26][C:27]1[C:28]([F:44])=[C:29]([O:34][C:35]2[CH:36]=[C:37]([CH:40]=[C:41]([Cl:43])[CH:42]=2)[C:38]#[N:39])[C:30]([Cl:33])=[CH:31][CH:32]=1.[C:45]([C:48]1[NH:52][C:51]([C:53](O)=[O:54])=[C:50]([Cl:56])[CH:49]=1)(=[O:47])[CH3:46].CCN(C(C)C)C(C)C>CN(C=O)C>[C:45]([C:48]1[NH:52][C:51]([C:53]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([O:34][C:35]3[CH:36]=[C:37]([C:38]#[N:39])[CH:40]=[C:41]([Cl:43])[CH:42]=3)[C:28]=2[F:44])=[O:54])=[C:50]([Cl:56])[CH:49]=1)(=[O:47])[CH3:46]

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 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 68483231HCID 68483231, compound

Product 1

HCID 59451479HCID 59451479, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (0.092 g, 0.241 mmol) was added to a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.050 g, 0.161 mmol), 5-acetyl-3-chloro-1H-pyrrole-2-carboxylic acid (0.030 g, 0.161 mmol) and DIPEA (0.042 mL, 0.241 mmol) in DMF (2 mL). The resulting solution was stirred overnight. The reaction mixture was partitioned between water and EtOAc. The organic layer was separated, dried over MgSO4 and evaporated to a residue. Purification was accomplished by reverse-phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.0127 g, 16%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 3.29 (s, 3H) 4.48 (d, J=5.36 Hz, 2H) 7.10 (s, 1H) 7.36-7.56 (m, 4H) 7.80 (s, 1H) 8.71 (t, J=5.22 Hz, 1H) 12.31 (br. s., 1H). LCMS: m/z 477.9 (M−1).

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customevaporated to a residue
  5. customPurification

Sources & evidence

ORD record
ord-2f2893814721458499c29cb74a2b4832
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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