Hydrochloric Acid → HCID 49821589, compound

HRID 511256Notes

Reaction equation

HRID 511256 reaction equation
[CH3:1][N:2]([S:36]([CH3:39])(=[O:38])=[O:37])[C:3]1[C:8]([CH2:9][NH:10][C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][N:14]=[C:13]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([P:28](=[O:35])([O:32]CC)[O:29][CH2:30][CH3:31])=[CH:24][CH:23]=3)[N:12]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.Cl>>[CH3:1][N:2]([S:36]([CH3:39])(=[O:38])=[O:37])[C:3]1[C:8]([CH2:9][NH:10][C:11]2[C:16]([C:17]([F:18])([F:19])[F:20])=[CH:15][N:14]=[C:13]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([P:28](=[O:32])([OH:35])[O:29][CH2:30][CH3:31])=[CH:26][CH:27]=3)[N:12]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 49822264HCID 49822264, compound

Product 1

HCID 49821589HCID 49821589, compound

Procedure

Diethyl [4-({4-[({2-[methyl(methylsulfonyl)amino]pyridin-3-yl}methyl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)phenyl]phosphonate (Example 2) in an excess of concentrated HCl (37%) and heated at 80° C. for 5 h. The reaction mixture was concentrated in vacuo and the residue purified by preparative HPLC (MDP) to afford the title compound (Example 40). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15 (t, J=6.9 Hz, 3H), 3.16 (s, 6H), 3.81 (ddd, J=14.7, 7.3, 7.1 Hz, 2H), 4.83 (d, J=5.6 Hz, 2H), 7.34-7.45 (m, 3H), 7.55 (dd, J=8.2, 3.2 Hz, 2H), 7.64-7.73 (m, 2H), 8.31 (d, J=0.8 Hz, 1H), 8.45 (dd, J=4.7, 1.9 Hz, 1H), 9.86 (s, 1H); MS (UPLC TOF): m/z 562.14 [MH+]; HPLC: tR=1.15 min (polar-3).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by preparative HPLC (MDP)

Sources & evidence

ORD record
ord-422f5714a1c740e0847fdc73125b0ede
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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