Diisopropylethylamine → HCID 59451475, compound

HRID 1874882Notes

Reaction equation

HRID 1874882 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Br:34][C:35]1[C:43]2[C:38](=[CH:39][C:40]([O:44][CH2:45][CH2:46][OH:47])=[CH:41][CH:42]=2)[NH:37][C:36]=1[C:48]([OH:50])=O.[NH2:51][CH2:52][C:53]1[C:54]([F:70])=[C:55]([O:60][C:61]2[CH:62]=[C:63]([CH:66]=[C:67]([Cl:69])[CH:68]=2)[C:64]#[N:65])[C:56]([Cl:59])=[CH:57][CH:58]=1>CN(C=O)C>[Br:34][C:35]1[C:43]2[C:38](=[CH:39][C:40]([O:44][CH2:45][CH2:46][OH:47])=[CH:41][CH:42]=2)[NH:37][C:36]=1[C:48]([NH:51][CH2:52][C:53]1[CH:58]=[CH:57][C:56]([Cl:59])=[C:55]([O:60][C:61]2[CH:62]=[C:63]([C:64]#[N:65])[CH:66]=[C:67]([Cl:69])[CH:68]=2)[C:54]=1[F:70])=[O:50]

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 59451578HCID 59451578, compound

Product 1

HCID 59451475HCID 59451475, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (0.061 g, 0.161 mmol) and DIPEA (0.028 mL, 0.161 mmol) were added to a solution of 3-bromo-6-[(2-hydroxyethyl)oxy]-1H-indole-2-carboxylic acid (0.048 g, 0.161 mmol) and 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.050 g, 0.161 mmol) in DMF (2 mL). This solution was stirred overnight at room temperature. The mixture was partitioned between water and EtOAc, followed by washing of the organic layer with a 15% solution of Na2CO3. The organic layer was separated and dried over MgSO4. The EtOAc was evaporated to yield a residue which was triturated in acetone to afford the title compound (0.059 g, 59%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.78 (s, 1H), 8.37 (t, 1H), 7.80 (s, 1H), 7.48-7.54 (m, 2H), 7.40-7.47 (m, 2H), 7.35 (d, 1H), 6.87 (s, 1H), 6.82 (d, 1H), 4.86 (t, 1H), 4.59 (d, 2H), 3.97 (t, 2H), 3.72 (q, 2H). MS m/z 592 (M+1).

Workup

  1. customThe mixture was partitioned between water and EtOAc
  2. washby washing of the organic layer with a 15% solution of Na2CO3
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customThe EtOAc was evaporated
  6. customto yield a residue which
  7. customwas triturated in acetone

Sources & evidence

ORD record
ord-2718155cb8cd45adb38867d16af88044
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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