Diisopropylethylamine → HCID 59451406, compound

HRID 1875142Notes

Reaction equation

HRID 1875142 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:23])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[Cl:24][C:25]1[CH:29]=[CH:28][NH:27][C:26]=1[C:30](O)=[O:31].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Cl:24][C:25]1[CH:29]=[CH:28][NH:27][C:26]=1[C:30]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]2[CH:18]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:16]=[C:13]([C:14]#[N:15])[CH:12]=2)[C:4]=1[F:23])=[O:31]

Participants

7

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 221800183-chloro-1H-pyrrole-2-carboxylic acidHCID 684835233-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile

Product 1

HCID 59451406HCID 59451406, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile (71.0 mg, 0.206 mmol), 3-chloro-1H-pyrrole-2-carboxylic acid (30.0 mg, 0.206 mmol) and diisopropylethyl amine (0.036 ml, 0.206 mmol) in DMF (3.0 ml) was added HATU (78 mg, 0.206 mmol) and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was diluted with EtOAc, washed with water and the solvent was removed. The crude material was purified via reverse phase HPLC to give 3-chloro-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-pyrrole-2-carboxamide (83 mg, 0.176 mmol, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.78 (t, 1H), 8.11 (s, 1H), 7.95 (t, 1H), 7.80 (s, 1H), 7.74 (s, 1H), 7.46-7.57 (m, 1H), 7.37 (t, 1H), 6.92 (t, 1H), 6.18 (t, 1H), 4.54 (d, 2H). LC-MS (ES+) m/z 472.12, [M+H].

Workup

  1. washwashed with water
  2. customthe solvent was removed
  3. customThe crude material was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-6959d2ec00e148f9a3df58cfca6cbf66
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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