Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → HCID 178476859, compound

HRID 511268Notes

Reaction equation

HRID 511268 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][C:16]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:15][C:14]=2[O:28][CH3:29])[N:3]=1.[NH2:30][C:31]1[CH:32]=[CH:33][C:34]([C@H:42]2[CH2:47][CH2:46][C@@H:45]([N:48]3[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]3)[CH2:44][CH2:43]2)=[C:35]2[C:39]=1[C:38](=[O:40])[N:37]([CH3:41])[CH2:36]2>>[CH3:29][O:28][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:13]=1[NH:12][C:4]1[N:3]=[C:2]([NH:30][C:31]2[CH:32]=[CH:33][C:34]([C@H:42]3[CH2:47][CH2:46][C@@H:45]([N:48]4[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]4)[CH2:44][CH2:43]3)=[C:35]3[C:39]=2[C:38](=[O:40])[N:37]([CH3:41])[CH2:36]3)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=1)[CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 178480927HCID 178480927, compound

Product 1

HCID 178476859HCID 178476859, compound

Procedure

This compound was prepared in a manner analogous to Example 87 using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate and 7-amino-2-methyl-4-[cis-4-(4-methylpiperazin-1-yl)cyclohexyl]-2,3-dihydro-1H-isoindol-1-one. 1H NMR (CD3OD, 400 MHz): δ=1.29 (t, J=7.07 Hz, 6 H), 1.72 (dd, J=12.76, 3.66 Hz, 2 H), 1.77-1.89 (m, 2 H), 1.92-2.04 (m, 2 H), 2.21 (d, J=12.13 Hz, 2 H), 2.81-2.91 (m, 2 H), 2.93 (s, 3 H), 3.19 (s, 3 H), 3.33-3.41 (m, 2 H), 3.45 (br. s., 3 H), 3.91 (s, 3 H), 4.05-4.15 (m, 4 H), 4.55 (s, 2 H), 6.99 (ddd, J=7.96, 2.40, 2.27 Hz, 1 H), 7.13 (t, J=2.02 Hz, 1 H), 7.45 (d, J=8.59 Hz, 1 H), 7.70 (d, J=8.08 Hz, 1 H), 8.36 (s, 1 H), 8.41 (br. s., 1 H). MS (ES+): m/z 760.30 [MH+]; HPLC: tR=1.18 minutes (UPLC TOF MS: polar—3 min).

Workup

  1. customHPLC: tR=1.18 minutes (UPLC TOF MS: polar—3 min)

Sources & evidence

ORD record
ord-7cb2d8617bc7455cb07485aa2083ac74
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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