Ethyl hydrogen (4-{[4-({2-(diethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → Ethyl hydrogen (4-{[4-({2-(ethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

HRID 2279738Notes

Reaction equation

[CH2:1]([N:3](CC)[C:4]([C:6]1[CH:11]=[C:10]([C:12]2[CH:13]=[N:14][N:15]([CH2:17][CH2:18][CH2:19][OH:20])[CH:16]=2)[CH:9]=[CH:8][C:7]=1[NH:21][C:22]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][N:25]=[C:24]([NH:32][C:33]2[CH:45]=[CH:44][C:36]([CH2:37][P:38](=[O:43])([OH:42])[O:39][CH2:40][CH3:41])=[CH:35][C:34]=2OC)[N:23]=1)=[O:5])[CH3:2].C(NC(C1C=C(C2C=NN(CCCO)C=2)C=CC=1NC1C(C(F)(F)F)=CN=C(NC2C=CC(CP(=O)(OCC)OCC)=CC=2)N=1)=O)C>>[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[C:10]([C:12]2[CH:13]=[N:14][N:15]([CH2:17][CH2:18][CH2:19][OH:20])[CH:16]=2)[CH:9]=[CH:8][C:7]=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:42])([OH:43])[O:39][CH2:40][CH3:41])=[CH:44][CH:45]=2)[N:23]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 86697678Ethyl hydrogen (4-{[4-({2-(diethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HCID 86697695diethyl (4-{[4-({2-(ethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate2×

Product 1

HCID 86697694Ethyl hydrogen (4-{[4-({2-(ethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonateYield 53%

Procedure

Prepared analogously to Compound 3A using diethyl (4-{[4-({2-(ethylcarbamoyl)-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate (Compound 10B, 589 mg, 872 μmol) to afford 296 mg of the title compound (53%). 1H NMR (400 MHz, CD3OD) δ 8.41 (br. s., 1H), 8.27 (s, 1H), 8.16 (s, 1H), 7.93 (s, 1H), 7.82 (d, J=1.5 Hz, 1H), 7.67 (d, J=8.6 Hz, 1H), 7.46 (d, J=8.1 Hz, 2H), 7.24 (d, J=7.6 Hz, 2H), 4.31 (t, J=6.8 Hz, 2H), 3.84 (t, J=6.9 Hz, 2H), 3.58 (t, J=6.1 Hz, 2H), 3.40 (q, J=7.1 Hz, 2H), 2.90-3.03 (m, 2H), 2.10 (t, J=6.3 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H), 1.14 (t, J=6.9 Hz, 3H). MS (ESI): m/z 648.70 [M+H]+. UPLC: tR=1.04 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record: ord-a4ade64679ec4ebf9dd39843f1cb6964
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133224B2

Reaction notes

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