Diisopropylethylamine → HCID 131732729, compound

HRID 1470664Notes

Reaction equation

HRID 1470664 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:28])([CH3:27])[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:19]([F:20])=[C:18]([F:21])[C:17]([C:22]([OH:24])=O)=[C:16]([F:25])[C:15]=2[F:26])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][O:30][C:31](=[O:41])[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([NH2:39])[C:33]=1[NH2:40].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:29][O:30][C:31](=[O:41])[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([NH:39][C:22]([C:17]2[C:18]([F:21])=[C:19]([F:20])[C:14]([C:11]3[CH:10]=[CH:9][C:8]([C:7]([CH3:28])([CH3:27])[O:6][SiH2:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:13][CH:12]=3)=[C:15]([F:26])[C:16]=2[F:25])=[O:24])[C:33]=1[NH2:40]

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 58073904Methyl 2,3-diamino-5-methylbenzoateHCID 131732727HCID 131732727, compound

Product 1

HCID 131732729HCID 131732729, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-(tert-butyl-dimethyl-silanyloxymethyl)-2,3,5,6-tetrafluoro-biphenyl-4-carboxylic acid (2.2 g, 5.3 mmol) in dry DMF (50 mL) was added 2,3-diamino-5-methyl-benzoic acid methyl ester (0.95 g, 5.3 mmol) and HATU (3.03 g, 7.9 mmol) followed by N,N-diisopropylethylamine (1 mL). The reaction mixture was stirred for 14 h at room temperature under nitrogen atmosphere. TLC shows completion of the reaction. The reaction mixture was quenched to crushed ice and the precipitate was filtered, washed with water and dried to get an off white solid (2.4 g, 80.80%) which was directly taken to the next step.

Workup

  1. customcompletion of the reaction
  2. customThe reaction mixture was quenched
  3. customto crushed ice
  4. filtrationthe precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-6d980c2456774003ae9a7a8fde7c35e6
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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