Dimethylamine → HCID 136334018, compound

HRID 1842728Notes

Reaction equation

HRID 1842728 reaction equation
[CH3:1][NH:2][CH3:3].[F:4][P-:5]([F:10])([F:9])([F:8])([F:7])[F:6].Cl/[C:12](/[C:18]1[CH:19]=[N:20][N:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=12)=[CH:13]\[CH:14]=[N+:15]([CH3:17])[CH3:16]>CO>[F:4][P-:5]([F:10])([F:9])([F:8])([F:7])[F:6].[CH3:1][N:2]([CH3:3])/[C:12](/[C:18]1[CH:19]=[N:20][N:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=12)=[CH:13]\[CH:14]=[N+:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 136334020HCID 136334020, compound2×

Product 1

HCID 136334018HCID 136334018, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethylamine (24.0 mL, 48.0 mmol, 2M in THF) was added in one portion to a suspension of (Z)—N-(3-chloro-3-(pyrazolo[1,5-a]pyridin-3-yl)allylidene)-N-methylmethanaminium hexafluorophosphate (Intermediate 71, 6.07 g, 16 mmol) in CH3OH (40 mL) at r.t. under N2. The resulting solution was stirred at r.t. for 0.25 h then stored in the freezer overnight. Crystals were produced and these were collected, washed with CH3OH at −50° C. and THF, then dried by suction under a stream of N2. Two crops of crystals were collected to give the title compound (5.29 g, 85%) as a beige crystalline solid; m/z: ES+ M+ 244.

Workup

  1. customthen stored in the freezer overnight
  2. customCrystals were produced
  3. customthese were collected
  4. washwashed with CH3OH at −50° C.
  5. dry with materialTHF, then dried by suction under a stream of N2
  6. customTwo crops of crystals were collected

Sources & evidence

ORD record
ord-c8fd7e8a7402412d81119061e931ad27
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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