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 178476807, compound

HRID 2279919Notes

Reaction equation

HRID 2279919 reaction equation
OCCCN1C=C(C2C=CC(NC3C(C(F)(F)F)=CN=C(NC4C=CC(CP(=O)(OCC)OCC)=CC=4OC)N=3)=C3C=2CN(C)C3=O)C=N1.[NH2:50][C:51]1[C:52]([C:58]([NH:60][CH3:61])=[O:59])=[N:53][C:54]([Br:57])=[CH:55][CH:56]=1.OP1(=O)CC2C=CC(=C(OC)C=2)NC2=NC(=C(C(F)(F)F)C=N2)NC2C=CC(=NC=2C(NC)=O)C2=CN(N=C2)CCCO1.Cl[C:106]1[C:111]([C:112]([F:115])([F:114])[F:113])=[CH:110][N:109]=[C:108]([NH:116][C:117]2[CH:131]=[CH:130][C:120]([CH2:121][CH2:122][CH2:123][CH2:124][PH:125](=[O:129])[O:126][CH2:127][CH3:128])=[CH:119][C:118]=2[O:132][CH3:133])[N:107]=1>>[Br:57][C:54]1[N:53]=[C:52]([C:58](=[O:59])[NH:60][CH3:61])[C:51]([NH:50][C:110]2[C:111]([C:112]([F:113])([F:115])[F:114])=[CH:106][N:107]=[C:108]([NH:116][C:117]3[CH:131]=[CH:130][C:120]([CH2:121][CH2:122][CH2:123][CH2:124][PH:125](=[O:129])[O:126][CH2:127][CH3:128])=[CH:119][C:118]=3[O:132][CH3:133])[N:109]=2)=[CH:56][CH:55]=1

Participants

5

Reactant 4

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 866976863-Amino-6-bromo-N-methylpicolinamideHCID 8669783310-hydroxy-14-methoxy-N-methyl-20-(trifluoromethyl)-9-oxa-4,5,16,18,22,25,28-heptaaza-10-phosphapentacyclo[21.2.2.212,15.12,5.117,21]hentriaconta-1(25),2(31),3,12,14,17(28),18,20,23,26,29-undecaene-24-carboxamide 10-oxideHCID 178476805HCID 178476805, compound2×

Product 1

HCID 178476807HCID 178476807, compound

Procedure

Prepared analogously to Compound 1B replacing Compound 1C with compound 6D and Compound 1 E with ethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)propylphosphinate (Compound 37C). 1H NMR (CDCl3, 400 MHz): δ 12.25 (s, 1H), 9.05 (d, J=8.8 Hz, 1H), 8.43 (s, 1H), 8.10 (d, J=4.8 Hz, 2H), 7.69 (br. s., 1H), 7.51 (d, J=8.8 Hz, 1H), 6.94 (t, J=1.8 Hz, 1H), 6.82 (td, J=1.8, 8.2 Hz, 1H), 3.98-4.13 (m, 2H), 3.92 (s, 3H), 3.13 (d, J=16.4 Hz, 2H), 3.05 (d, J=5.3 Hz, 3H), 1.62-1.68 (m, 4H), 1.31 (t, J=7.1 Hz, 3H), 0.98-1.04 (m, 3H). MS (ESI): m/z 645.62/647.56 [M+H]+. UPLC: tR=1.47 min (UPLC-SQD: analytical—2 min).

Workup

  1. customtR=1.47 min (UPLC-SQD: analytical—2 min)

Sources & evidence

ORD record
ord-5c280d9e16f34189a9b5e398dd278749
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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