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}benzyl)phosphonate → Sodium ethyl (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}benzyl)phosphonate

HRID 2279707Notes

Reaction equation

HRID 2279707 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:45]=[CH:44][C:36]([CH2:37][P:38](=[O:43])([O-:42])[O:39][CH2:40][CH3:41])=[CH:35][C:34]=4OC)[N:23]=3)=[C:14]3[C:18]=2[CH2:17][N:16]([CH3:19])[C:15]3=[O:20])[CH:7]=[N:6]1.[Na+:48].OCCCN1C=C(C2C=CC(NC3C(C(F)(F)F)=CN=C(NC4C=CC(CP(=O)(OCC)OCC)=CC=4)N=3)=C3C=2CN(C)C3=O)C=N1>>[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:30])([F:31])[F:29])=[CH:26][N:25]=[C:24]([NH:32][C:33]4[CH:34]=[CH:35][C:36]([CH2:37][P:38](=[O:42])([O-:43])[O:39][CH2:40][CH3:41])=[CH:44][CH:45]=4)[N:23]=3)=[C:14]3[C:18]=2[CH2:17][N:16]([CH3:19])[C:15]3=[O:20])[CH:7]=[N:6]1.[Na+:48]

Participants

3

Reactant 2

HCID 58292962Diethyl (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}benzyl)phosphonate2×HCID 86697675Sodium ethyl (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

Product 1

HCID 86697677Sodium ethyl (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}benzyl)phosphonate

Procedure

Prepared analogously to Compound 1A using 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}benzyl)phosphonate (Compound 2B). 1H NMR (400 MHz, DMSO-d6) δ 10.66 (br s, 1H), 9.74 (s, 1H), 8.46-9.05 (m, 2H), 8.41 (s, 1H), 8.00 (br s, 1H), 7.82 (s, 1H), 7.10-7.53 (m, 4H), 4.62 (s, 2H), 4.20 (t, J=6.4 Hz, 2H), 3.70 (quin, J=7 Hz, 2H), 3.45 (t, J=6.1 Hz, 2H), 3.11 (s, 3H), 2.84 (d, J=20.2 Hz, 2H), 1.96 (quin, J=6.3 Hz, 2H), 1.01 (t, J=6.7 Hz, 3H) [OH proton obscured]. HRMS (ESI): m/z 646.14 [M+H]+. UPLC: tR=1.16 min (UPLC-TOF: polar—3 min).

Workup

  1. customtR=1.16 min (UPLC-TOF: polar—3 min)

Sources & evidence

ORD record
ord-3d51bd4b0ebb4e6e8fdd0591220fd1e2
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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