(1S)-1-phenylpropan-1-amine → HCID 44405474, compound

HRID 2113589Notes

Reaction equation

HRID 2113589 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].[C:23]1([C@@H:29]([NH2:32])[CH2:30][CH3:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[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:32][C@H:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:30][CH3:31])[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 6993773(1S)-1-phenylpropan-1-amineHCID 185489534-(3-Chloro-4-fluorophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 44405474HCID 44405474, compoundYield 40.4%

Conditions

Temperature
185 °C

Procedure

Following the procedure described above in Example 51, 4-(3-Chloro-4-fluoro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile (0.15 g, 0.47 mmol) was reacted with (s)-(−)-1-phenylpropylamine (2.0 mL, 1.86 g, 13.8 mmol) in a sealed vial heated in a microwave reactor at 185° C. for 90 min. The crude product was purified by preparative HPLC and lyophilized to give a fluffy, yellow solid (82 mg, 40.4% yield): 1H NMR (400 MHz, MeOD) δ ppm 0.99 (t, J=7.45 Hz, 3 H) 1.78-2.01 (m, 2 H) 4.58 (t, J=7.20 Hz, 1 H) 6.72 (s, 1 H) 7.14-7.37 (m, 7 H) 7.40 (dd, J=2.53 Hz, 1 H) 8.22 (s, 1 H) 8.81 (s, 1 H); HRMS (ESI+) calcd for C24H19ClFN5 432.13858; found (MH+) 432.1391.

Workup

  1. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-ebbd3c5587904908be04be47b5a0d775
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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