(S)-(+)-1-Aminopropan-2-ol → HCID 69317960, compound

HRID 2113593Notes

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][C@@H:25]([OH:27])[CH3:26]>C1COCC1>[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][C@@H:25]([OH:27])[CH3:26])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:21]#[N:22])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 140 °C

Procedure

Following the procedure described above in Example 51, 4-(3-Chloro-4-fluoro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile (0.10 g, 0.32 mmol) was reacted with (S)-1-amino-2-propanol (0.47 g, 6.32 mmol) in 2 mL of THF. The reaction mixture was heated up in a sealed vial in a microwave reactor at 140° C. for 40 min. The crude product was purified by preparative HPLC and lyophilized to give a yellow solid (20.8 mg, 17.7% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 0.93 (d, J=6.32 Hz, 3 H) 2.96-3.03 (m, 2 H) 3.68 (s, 1 H) 4.58 (s, 1 H) 6.46 (m, 1 H) 6.80 (s, 1 H) 7.06-7.17 (m, 1 H) 7.21-7.33 (m, 1 H) 7.33-7.47 (m, 1 H) 8.05 (s, 1 H) 8.62 (s, 1 H) 9.44 (s, 1 H); HRMS (ESI+) calcd for C18H15ClFN5O 372.10219, found (MH+) 372.1019.

Workup

customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-73bea914004b4973831a173194986c6f
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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