4-Morpholinecarbonyl chloride → HCID 10287377, compound

HRID 1265074Notes

Reaction equation

HRID 1265074 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:12]([CH3:14])=[C:11]([CH3:15])[N:10]=[C:9]([NH2:16])[C:8]=2[N:7]=[C:6]1[CH2:17][O:18][CH2:19][CH3:20].[N:21]1([C:27](Cl)=[O:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[NH2:16][C:9]1[C:8]2[N:7]=[C:6]([CH2:17][O:18][CH2:19][CH3:20])[N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:27]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:28])[C:13]=2[C:12]([CH3:14])=[C:11]([CH3:15])[N:10]=1

Participants

3

Reactant 2

HCID 848104-Morpholinecarbonyl chlorideHCID 219738361-(3-aminopropyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 10287377HCID 10287377, compoundYield 74.7%

Procedure

Using the general method of Example 13 Part G, 1-(3-aminopropyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (1.00 g, 3.6 mmol) was reacted with 4-morpholinylcarbonyl chloride (0.46 mL, 40 mmol) to provide 1.05 g of N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}morpholine-4-carboxamide as an off white solid, m.p. 140.5-142.2° C. Analysis: Calculated for C19H30N6O3.1.00 H2O: %C, 55.86; %H, 7.90; %N, 20.57; Found: %C, 55.60; %H, 7.87; %N, 20.59. 1H NMR (Bruker 300 MHz, DMSO-d6) δ6.64 (t, J=5.6 Hz, 1 H), 5.75 (s, 2 H), 4.62 (s, 2 H), 4.28 (t, J=8.1 Hz, 2 H), 3.54 (t, J=4.9 Hz, 4 H), 3.51 (q, J=6.9 Hz, 2 H), 3.25 (t, J=4.9 Hz, 4 H), 3.15 (q, J=5.6 Hz, 2 H), 2.36 (s, 3 H), 2.30 (s, 3 H), 1.87 (p, J=8.1 Hz, 2 H), 1.13 (t, J=7.5 Hz, 3 H). MS(CI) m/e 276 (M+H).

Sources & evidence

ORD record
ord-223a76b916d24cc483358ac920d70597
Source dataset
uspto-grants-2003_04
Patent number
US06545017B1

Reaction notes

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