N,N-Dimethyl-1,3-propanediamine → HCID 69316400, compound

HRID 2113585Notes

Reaction equation

HRID 2113585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][N:16]=[C:17](F)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:21]#[N:22])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][NH2:28]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][N:16]=[C:17]([NH:28][CH2:27][CH2:26][CH2:25][N:24]([CH3:29])[CH3:23])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:21]#[N:22])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 185489534-(3-Chloro-4-fluorophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 69316400HCID 69316400, compoundYield 44%

Procedure

Following the procedure described above in Example 34, 4-(3-Chloro-4-fluoro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile was reacted with N1,N1-dimethylpropane-1,3-diamine. The crude product was purified by flash column chromatography (15% methanol in methylene chloride) to give a yellow solid (0.040 g, 44%). 1H NMR (400 MHz, chloroform-D) δ ppm 1.8 (m, 2 H) 2.3 (s, 6 H) 2.4 (t, J=6.4 Hz, 2 H) 3.2 (t, J=6.6 Hz, 2 H) 3.5 (s, 1 H) 6.3 (s, 1 H) 7.1 (m, 2 H) 7.2 (t, J=8.6 Hz, 1 H) 7.3 (dd, J=6.3, 2.8 Hz, 1 H) 8.4 (s, 1 H) 9.0 (s, 1 H).

Workup

  1. customThe crude product was purified by flash column chromatography (15% methanol in methylene chloride)

Sources & evidence

ORD record
ord-8b611d9bc33a469fa604a7feaa525f81
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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