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 → HCID 86697727, compound

HRID 2279776Notes

Reaction equation

HRID 2279776 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]=2C[N:16](C)[C:15]3=[O:20])[CH:7]=[N:6]1.NC1C=CC(C2C=NN(CCCO)C=2)=CC=1[C:53](NOC)=[O:54]>>[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:29])[F:30])=[CH:26][N:25]=[C:24]([NH:32][C:33]4[CH:47]=[CH:46][C:36]([CH2:37][P:38](=[O:45])([O:39][CH2:40][CH3:41])[O:42][CH2:43][CH3:44])=[CH:35][C:34]=4[O:48][CH3:49])[N:23]=3)=[C:14]([C:15](=[O:20])[NH:16][O:54][CH3:53])[CH:18]=2)[CH:7]=[N:6]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 866977282-amino-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methoxybenzamide2×

Product 1

HCID 86697727HCID 86697727, compoundYield 28%

Procedure

Prepared analogously to Compound 1B replacing Compound 1C with 2-amino-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methoxybenzamide (Compound 26C, 169 mg, 583 μmol) to afford 114 mg of the title compound (28%). 1H NMR (400 MHz, CD3OD) δ=8.33 (s, 1H), 8.14 (s, 1H), 7.96 (d, J=0.5 Hz, 1H), 7.92 (d, J=8.1 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 7.71 (dd, J=2.2, 8.7 Hz, 1H), 7.00 (t, J=2.2 Hz, 1H), 6.81 (d, J=8.3 Hz, 1H), 4.31 (t, J=7.0 Hz, 2H), 3.99-4.08 (m, 4H), 3.90 (s, 3H), 3.81 (s, 3H), 3.58 (t, J=6.1 Hz, 2H), 3.24 (d, J=21.0 Hz, 2H), 2.10 (quin. J=6.6 Hz, 2H), 1.24 (t, J=7.1 Hz, 6H). MS (ESI): m/z=708.72 [M+H]+. UPLC: tR=1.13 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record
ord-7430dd1249d94afb8a16945ea776fe5d
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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