Diethyl (4-{[4-({7-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → diethyl (4-{[4-({2-(ethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([NH:21][C:22]3[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][N:25]=[C:24]([NH:32][C:33]4[CH:47]=[CH:46][C:36]([CH2:37][P:38](=[O:45])([O:42][CH2:43][CH3:44])[O:39][CH2:40][CH3:41])=[CH:35][C:34]=4OC)[N:23]=3)=[C:14]3[C:18]=2C[N:16]([CH3:19])[C:15]3=[O:20])[CH:7]=[N:6]1.N[C:51]1C=CC(C2C=NN(CCCO)C=2)=CC=1C(NCC)=O>>[CH2:19]([NH:16][C:15]([C:14]1[CH:18]=[C:10]([C:8]2[CH:7]=[N:6][N:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH:9]=2)[CH:11]=[CH:12][C:13]=1[NH:21][C:22]1[C:27]([C:28]([F:29])([F:30])[F:31])=[CH:26][N:25]=[C:24]([NH:32][C:33]2[CH:34]=[CH:35][C:36]([CH2:37][P:38](=[O:45])([O:39][CH2:40][CH3:41])[O:42][CH2:43][CH3:44])=[CH:46][CH:47]=2)[N:23]=1)=[O:20])[CH3:51]Participants
3
Reactant 2
Product 1
Procedure
Prepared analogously to Compound 1B replacing Compound 1C with 2-amino-N-ethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide (Compound 9C, 455 mg, 1.07 mmol) to afford 589 mg of the title compound (81%). 1H NMR (400 MHz, CD3OD) δ 8.42 (d, J=8.8 Hz, 1H), 8.31 (s, 1H), 8.13 (s, 1H), 7.96 (s, 1H), 7.84 (d, J=2.0 Hz, 1H), 7.68 (dd, J=2.2, 8.7 Hz, 1H), 7.55 (d, J=8.3 Hz, 2H), 7.23 (dd, J=2.6, 8.7 Hz, 2H), 4.31 (d, J=13.6 Hz, 2H), 3.97-4.08 (m, 4H), 3.57 (t, J=6.2 Hz, 2H), 3.38-3.42 (m, 2H), 3.18-3.25 (m, 2H), 2.10 (quin, J=6.5 Hz, 2H), 1.17-1.26 (m, 9H). MS (ESI): m/z 676.78 [M+H]+. UPLC: tR=1.18 min (UPLC-SQD: analytical—2 min).
Sources & evidence
- ORD record
- ord-f5f682917aa0494ba894575364194436
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133224B2
Reaction notes
Loading…