Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate → HCID 178476872, compound

HRID 1947967Notes

Reaction equation

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

Participants

Reactant 2

HCID 86654003Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

HCID 178468154HCID 178468154, compound2×

Product 1

HCID 178476872HCID 178476872, compound

Procedure

The title product was prepared according to the procedure for Example 102 using diethyl(4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate (40.0 mg, 0.0944 mmol) and 7-amino-4-(trans-4-ethoxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one (Compound 166B). 1H NMR (DMSO-d6, 400 MHz): δ=1.11 (t, J=6.95 Hz, 3H), 1.18 (t, J=6.95 Hz, 6H), 1.21-1.33 (m, 2H), 1.54-1.68 (m, 2H), 1.80 (d, J=12.63 Hz, 2H), 2.09 (dd, J=12.63, 3.28 Hz, 2H), 3.08 (s, 3H), 3.18-3.27 (m, 2H), 3.49 (q, J=6.99 Hz, 2H), 3.91-4.01 (m, 4H), 4.52 (s, 2H), 7.26 (dd, J=8.72, 1.89 Hz, 2H), 7.40 (d, J=8.59 Hz, 1H), 7.56 (br. s., 2H), 8.45 (s, 1H), 8.67 (s, 1H), 9.89 (s, 1H), 10.58 (br. s., 1H). MS (ES+): m/z=676.25 [MH+] (TOF, polar).

Sources & evidence

ORD record: ord-6700607b2ffc467b884193fd92da6e5c
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399433B2

Reaction notes

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