Acetonitrile → HCID 10364592, compound

HRID 2113983Notes

Reaction equation

HRID 2113983 reaction equation
NC[C:3]1[S:4][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19](F)=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=3)[N:10]=2)=[C:6]([CH3:8])[N:7]=1.[CH3:26][O:27][CH2:28][CH2:29][OH:30].C[C:32]#[N:33]>>[CH3:26][O:27][CH2:28][CH2:29][O:30][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:11]2[N:10]=[C:9]([C:5]3[S:4][C:3]([NH:33][CH3:32])=[N:7][C:6]=3[CH3:8])[CH:14]=[CH:13][N:12]=2)=[CH:17][C:18]=1[N+:23]([O-:25])=[O:24]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 80192-MethoxyethanolHCID 67269584HCID 67269584, compound

Product 1

HCID 10364592HCID 10364592, compound

Procedure

By alkylation of [4-(2-aminomethyl-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(4-fluoro-3-nitrophenyl)-amine with 2-methoxy-ethanol. Yellow solid. Anal. RP-HPLC: tR=12.8 min (10-70% MeCN, purity>90%). 1H-NMR (DMSO-D6) δ: 2.41 (s, 3H, CH3), 2.86 (d, 3H, J=4.5 Hz, CH3), 3.24 (s, 3H, CH3), 3.66 (m, 2H, CH2), 4.23 (m, 2H, CH2), 6.93 (d, 1H, J=6.0 Hz, pyrimidinyl-H), 7.32 (d, 1H, J=5.0 Hz, Ph-H), 7.79 (m, 1H, Ph-H), 8.08 (d, 1H, J=5.0 Hz, Ph-H), 8.35 (d, 1H, J=5.0 Hz, pyrimidinyl-H), 8.54 (m, 1H, NH), 9.68 (s, 1H, NH). MS (ESI+) m/z 417.08 [M+H]+ (C18H20N6O4S requires 416.46).

Sources & evidence

ORD record
ord-9b82296cc7704fe4812e1de67dff316b
Source dataset
uspto-grants-2008_10
Patent number
US07432260B2

Reaction notes

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