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-({4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-3-methyl-2-(methyl carbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 2279790Notes

Reaction equation

HRID 2279790 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]([CH3:19])[C:15]3=[O:20])[CH:7]=[N:6]1.NC1C(C(NC)=O)=C(C)C(C2C=NN(CCCO)C=2)=CC=1>>[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:29])([F:30])[F:31])=[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]([C:15](=[O:20])[NH:16][CH3:19])[C:18]=2[CH3:17])[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 678188446-amino-3-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N,2-dimethyl benzamide2×

Product 1

HCID 86697738Diethyl (4-{[4-({4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-3-methyl-2-(methyl carbamoyl)phenyl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Procedure

Prepared analogously to Compound 1B replacing Compound C with 6-amino-3-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N,2-dimethyl benzamide (Compound 29C). 1H NMR (CD3OD, 400 MHz): δ=8.28 (s, 1H), 7.92 (s, 1H), 7.89 (d, J=8.3 Hz, 1H), 7.72 (s, 1H), 7.63 (d, J=8.4 Hz, 1H), 7.48 (d, J=8.3 Hz, 1H), 6.92 (t, J=2.0 Hz, 1H), 6.60 (d, J=7.4 Hz, 1H), 4.35 (t, J=6.8 Hz, 2H), 4.00 (m, 4H), 3.89 (s, 3H), 3.60 (t, J=6.1 Hz, 2H), 3.16 (d, J=21.5 Hz, 2H), 2.85 (s, 3H), 2.37 (s, 3H), 2.12 (m, 2H), 1.22 (t, J=7.1 Hz, 6H). MS (ESI): m/z=706.58 [M+H]+. HPLC: tR=3.47 min (ZQ3: polar—5 min).

Workup

  1. customHPLC: tR=3.47 min (ZQ3: polar—5 min)

Sources & evidence

ORD record
ord-0d81a494dc3246508bbd1505fdb6d230
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

Loading…