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 86697712, compound

HRID 2279760Notes

Reaction equation

HRID 2279760 reaction equation
OCCCN1C=C(C2C=CC(N[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)=C3C=2CN(C)C3=O)C=N1.[NH2:50][C:51]1[C:52]([C:67]([NH:69][CH3:70])=[O:68])=[N:53][C:54]([C:57]2[CH:58]=[N:59][N:60]([CH2:62][CH:63]([CH3:66])[CH2:64][OH:65])[CH:61]=2)=[CH:55][CH:56]=1>>[OH:65][CH2:64][CH:63]([CH3:66])[CH2:62][N:60]1[CH:61]=[C:57]([C:54]2[N:53]=[C:52]([C:67](=[O:68])[NH:69][CH3:70])[C:51]([NH:50][C:26]3[C:27]([C:28]([F:29])([F:30])[F:31])=[CH:22][N:23]=[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:25]=3)=[CH:56][CH:55]=2)[CH:58]=[N:59]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 866977133-amino-6-[1-(3-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide2×

Product 1

HCID 86697712HCID 86697712, compound

Procedure

Prepared analogously to Compound 1B using replacing compound 1C with 3-amino-6-[1-(3-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide (Compound 18C). 1H NMR (CD3OD, 400 MHz): δ=8.92 (br. s., 1H) 8.51 (s, 1H) 8.37 (br. s., 1H) 8.31 (s, 1H) 7.77 (d, J=8.8 Hz, 1H) 7.54 (d, J=7.8 Hz, 1H) 7.17 (s, 1H) 7.04 (d, J=7.8 Hz, 1H) 4.29 (dd, J=13.8, 6.44 Hz, 1H) 4.00-4.16 (m, 5H) 3.89 (s, 3H) 3.47 (d, J=5.6 Hz, 2H) 3.37 (d, J=21.7 Hz, 2H) 3.00 (s, 3H) 2.26 (dq, J=12.8, 6.4 Hz, 1H) 1.27 (t, J=7.1 Hz, 6H) 0.94 (d, J=6.8 Hz, 3H). MS (ESI): m/z=707.70 [M+H]+. UPLC: tR=1.29 min (UPLC-SQD: analytical—2 min).

Workup

  1. customtR=1.29 min (UPLC-SQD: analytical—2 min)

Sources & evidence

ORD record
ord-f1d856be6eb8413f8f96d98094b81cc1
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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