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-({3-chloro-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxy benzyl)phosphonate

HRID 2279785Notes

Reaction equation

HRID 2279785 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]=4[O:48][CH3:49])[N:23]=3)=[C:14]3[C:18]=2[CH2:17][N:16](C)[C:15]3=[O:20])[CH:7]=[N:6]1.NC1C(C(NC)=O)=C([Cl:61])C(C2C=NN(CCCO)C=2)=CC=1>>[Cl:61][C:18]1[C:14]([C:15](=[O:20])[NH:16][CH3:17])=[C:13]([NH:21][C:22]2[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][N:25]=[C:24]([NH:32][C:33]3[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]=3[O:48][CH3:49])[N:23]=2)[CH:12]=[CH:11][C:10]=1[C:8]1[CH:7]=[N:6][N:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH:9]=1

Participants

3

Reactant 2

HCID 58292892Diethyl (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)phosphonateHCID 866977356-amino-2-chloro-3-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylbenzamide2×

Product 1

HCID 86697734Diethyl (4-{[4-({3-chloro-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-(methylcarbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxy benzyl)phosphonateYield 3%

Procedure

Prepared analogously to Compound 1B replacing Compound 1C with 6-amino-2-chloro-3-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylbenzamide (Compound 28C, 274 mg, 887 μmol) to afford 21 mg of the title compound (3%). 1H NMR (400 MHz, CD3OD) δ=8.31 (s, 1H), 8.17 (s, 1H), 7.93 (s, 1H), 7.84 (d, J=7.8 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.65 (d, J=8.6 Hz, 1H), 6.94 (t, J=2.0 Hz, 1H), 6.66 (d, J=7.8 Hz, 1H), 4.34 (t, J=6.8 Hz, 2H), 3.95-4.05 (m, 4H), 3.89 (s, 3H), 3.59 (t, J=6.2 Hz, 2H), 3.20 (s, 1H), 3.14 (s, 1H), 2.86 (s, 3H), 2.11 (quin, J=6.6 Hz, 2H), 1.22 (t, J=7.1 Hz, 6H). MS (ESI): m/z=726.19 [M+H]+. UPLC: tR=1.32 min (UPLC-TOF: polar—3 min).

Sources & evidence

ORD record
ord-da1c5d42f1774db794793bf0c0a69fca
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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