N,N-Dimethyl-1,3-propanediamine → N'-[5-(3-Ethanesulfonyl-phenyl)-3-methyl-9H-dipyrido[2,3-b;4',3'-d]pyrrol-8-yl]-N,N-dimethyl-propane-1,3-diamine

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethyl-1,3-propanediamine	HCID 7993	—
Reactant	8-Chloro-5-(3-ethanesulfonyl-phenyl)-3-methyl-9H-dipyrido[2,3-b; 4',3'-d]pyrrole	HCID 16123214	—
Product	N'-[5-(3-Ethanesulfonyl-phenyl)-3-methyl-9H-dipyrido[2,3-b;4',3'-d]pyrrol-8-yl]-N,N-dimethyl-propane-1,3-diamine	HCID 16123215	—

Reaction Steps

Compound 32 (16 mg, 0.041 mmol) was heated with 3-dimethylamino-1-propylamine (1 mL) at 206° C. in the microwave for 30 min. Purification by prep-HPLC gave 10.2 (55%) of the title compound as a pale yellow solid. 1H NMR (400 MHz, MeOD-d4): δ 8.65 (br s, 1H), 8.17 (s, 1H), 8.12 (d, 1H, J=7.6 Hz), 7.98 (d, 1H, J=7.6 Hz), 7.91 (t, 1H, J=7.6 Hz), 7.67 (s, 1H), 7.66 (s, 1H), 3.80 (t, 2H, J=6.8 Hz), 3.28-3.43 (m, 4H), 2.96 (s, 6H), 2.29-2.38 (m, 5H), 1.28 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C24H29N5O2S, 452; found 452.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08318939B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-1b275bb5079748eeb2fdc8c63165f26f
Source note	uspto-grants-2012_11