Diethyl P-[(4-aminophenyl)hydroxymethyl]phosphonate → HCID 58292911, compound
Reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([P:32](=[O:39])([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35])[OH:31])=[CH:26][CH:25]=1>>[CH3:14][NH:13][C:11]([C:10]1[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=1[NH:8][C:6]1[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=[C:2]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH:30]([P:32](=[O:39])([O:33][CH2:34][CH3:35])[O:36][CH2:37][CH3:38])[O:31][CH2:5][C:19]([F:22])([F:21])[F:20])=[CH:26][CH:25]=2)[N:7]=1)=[O:12]Participants
Procedure
The title compound was prepared using the procedure for Example 102 with 2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide (40 mg, 0.12 mmol) and diethyl [(4-aminophenyl)(hydroxy)methyl]-phosphonate (37.6 mg, 0.15 mmol). The crude product was purified by prep TLC (5% 7 N ammonia in MeOH in DCM) to give 13.8 mg of the desired product (yield: 18%). 1H NMR (CD3OD, 400 MHz): δ=1.22 (t, J=7.6 Hz, 3 H), 1.31 (t, J=7.2 Hz, 3 H), 2.90 (s, 3 H), 3.91-4.08 (m, 4 H), 4.12-4.18 (m, 2 H), 4.95 (d, J=14.8 Hz, 1 H), 7.18 (t, J=7.2 Hz, 1 H), 7.36 (d, J=8.4 Hz, 2 H), 7.49 (dt, J=2.4, 7.6 Hz, 1 H), 7.64 (dd, J=1.6, 7.6 Hz, 1 H), 7.68 (d, J=7.6 Hz, 2 H), 8.35 (s, 1 H), 8.43 (m, 1 H). MS (ES+): m/z 636.14 [MH+]. HPLC: tR=1.59 min (UPLC TOF, polar—3 min).
Workup
- customThe title compound was prepared
- customThe crude product was purified by prep TLC (5% 7 N ammonia in MeOH in DCM)
Sources & evidence
- ORD record
- ord-774b6c6bfbca452cab953ce9c965b1fd
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096624B2
Reaction notes
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