Diisopropylethylamine → HCID 178432443, compound

HRID 1875069Notes

Reaction equation

HRID 1875069 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Br:9])=[CH:7][CH:8]=1.[Br:21][C:22]1[N:23]=[C:24]([CH3:30])[NH:25][C:26]=1[C:27](O)=[O:28].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>CN(C=O)C>[Br:21][C:22]1[N:23]=[C:24]([CH3:30])[NH:25][C:26]=1[C:27]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([C:14]#[N:15])[CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:4]=1[F:20])=[O:28]

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 671971663-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 1784324484-bromo-2-methyl-1H-imidazole-5-carboxylic acid

Product 1

HCID 178432443HCID 178432443, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.050 g, 0.141 mmol), 4-bromo-2-methyl-1H-imidazole-5-carboxylic acid (0.029 g, 0.141 mmol), HATU (0.064 g, 0.169 mmol) and DIPEA (0.029 mL, 0.169 mmol) in DMF (1 mL) was stirred at RT overnight. The reaction mixture was extracted with EtOAc and water. The organic layer was dried over sodium sulfate and concentrated. The residue was purified by preparative LCMS (acetonitrile:water with 0.1% formic acid) to give the title compound (15 mg, 19.6%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.17 (br. s., 1H), 7.77 (s, 1H), 7.57 (d, 1H), 7.45 (s, 1H), 7.40 (d, 1H), 7.25 (t, 1H), 4.18-4.59 (m, 2H), 2.21 (s, 3H). ES MS: m/z 541, 543.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by preparative LCMS (acetonitrile:water with 0.1% formic acid)

Sources & evidence

ORD record
ord-50f5c9a455854583a64c76181a0ebe3d
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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