Diisopropylethylamine → HCID 59451561, compound

HRID 1874883Notes

Reaction equation

HRID 1874883 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.[OH:34][CH2:35][CH2:36][O:37][C:38]1[CH:46]=[C:45]2[C:41]([CH:42]=[C:43]([C:47]([OH:49])=O)[NH:44]2)=[CH:40][CH:39]=1.[NH2:50][CH2:51][C:52]1[C:53]([F:69])=[C:54]([O:59][C:60]2[CH:61]=[C:62]([CH:65]=[C:66]([Cl:68])[CH:67]=2)[C:63]#[N:64])[C:55]([Cl:58])=[CH:56][CH:57]=1>CN(C=O)C>[Cl:58][C:55]1[CH:56]=[CH:57][C:52]([CH2:51][NH:50][C:47]([C:43]2[NH:44][C:45]3[C:41]([CH:42]=2)=[CH:40][CH:39]=[C:38]([O:37][CH2:36][CH2:35][OH:34])[CH:46]=3)=[O:49])=[C:53]([F:69])[C:54]=1[O:59][C:60]1[CH:61]=[C:62]([C:63]#[N:64])[CH:65]=[C:66]([Cl:68])[CH:67]=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 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 59451410HCID 59451410, compound

Product 1

HCID 59451561HCID 59451561, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (0.070 g, 0.186 mmol) and DIPEA (0.024 mL, 0.186 mmol) were added to a solution 6-[(2-hydroxyethyl)oxy]-1H-indole-2-carboxylic acid (0.041 g, 0.186 mmol) and 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.057 g, 0.186 mmol) in DMF. This solution was stirred 2 h at room temperature. The mixture was partitioned between water and EtOAc, the organic layer was separated, washed with a 15% solution of Na2CO3, dried over MgSO4 and filtered. The EtOAc was evaporated to yield a residue which upon trituration in EtOAc afforded the title compound (0.041 g, 42%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.38 (s, 1H), 8.88 (t, 1H), 7.80 (s, 1H), 7.43-7.53 (m, 4H), 7.37 (t, 1H), 7.08 (s, 1H), 6.85 (s, 1H), 6.68 (d, 1H), 4.83 (t, 1H), 4.53 (d, 2H), 3.94 (t, 2H), 3.71 (q, 2H). MS m/z 512 (M−1).

Workup

  1. customThe mixture was partitioned between water and EtOAc
  2. customthe organic layer was separated
  3. washwashed with a 15% solution of Na2CO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe EtOAc was evaporated
  7. customto yield a residue which upon trituration in EtOAc

Sources & evidence

ORD record
ord-eb5f577c9cde4c83a55ecddec3a6c3c1
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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