Dimethylamine → HCID 86669669, compound

HRID 1623926Notes

Reaction equation

HRID 1623926 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7]([C:9]1[C:10]2[CH2:11][C@H:12]3[CH2:24][C@H:13]3[C:14]=2[N:15]([C:17]2[CH:22]=[N:21][CH:20]=[C:19](Cl)[N:18]=2)[N:16]=1)=[O:8])([CH3:5])[CH3:4].[CH3:25][NH:26][CH3:27]>C1COCC1>[OH:1][CH2:2][C:3]([NH:6][C:7]([C:9]1[C:10]2[CH2:11][C@H:12]3[CH2:24][C@H:13]3[C:14]=2[N:15]([C:17]2[CH:22]=[N:21][CH:20]=[C:19]([N:26]([CH3:27])[CH3:25])[N:18]=2)[N:16]=1)=[O:8])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86669670HCID 86669670, compound

Product 1

HCID 86669669HCID 86669669, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

(1aR,5aR)-2-(6-Chloro-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (25 mg, 0.072 mmol) was added to a 2.0 M THF solution of dimethylamine (0.719 mL, 1.438 mmol). The reaction was heated under microwave irradiation for 30 min at 100° C., then for 60 min at 110° C. The mixture was concentrated and purified by silica gel flash chromatography to provide the title compound (18 mg) as a white solid. LCMS m/z=357.4 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.45 (td, J=4.7, 3.3 Hz, 1H), 1.21 (td, J=7.8, 4.8 Hz, 1H), 1.41 (s, 3H), 1.42 (s, 3H), 2.22-2.28 (m, 1H), 2.70-2.75 (m, 1H), 2.90 (d, J=16.8 Hz, 1H), 3.00 (dd, J=16.6, 6.3 Hz, 1H), 3.18 (s, 6H), 3.70 (s, 2H), 4.87 (bs, 1H), 6.98 (s, 1H), 7.93 (s, 1H), 8.41 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-5519fb324098466c9c383166a76b164b
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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