3-Amino-1-propanol → HCID 69211249, compound

HRID 2113587Notes

Reaction equation

HRID 2113587 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].[NH2:23][CH2:24][CH2:25][CH2:26][OH:27]>>[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:23][CH2:24][CH2:25][CH2:26][OH:27])[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 90863-Amino-1-propanolHCID 185489534-(3-Chloro-4-fluorophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 69211249HCID 69211249, compoundYield 55%

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 3-aminopropan-1-ol. The crude product was purified by flash column chromatography (1% methanol in methylene chloride) to give a yellow solid (0.048 g, 55%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.8 (m, 2 H) 3.3 (d, J=6.3 Hz, 4 H) 3.5 (m, 2 H) 6.9 (m, 1 H) 7.0 (s, 1 H) 7.4 (m, 1 H) 7.5 (t, J=9.2 Hz, 1 H) 7.6 (m, 1 H) 8.3 (s, 1 H) 8.8 (s, 1 H).

Workup

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

Sources & evidence

ORD record
ord-d7ebd1914c124667a48cb583efc800c5
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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