2-Amino-5-fluoro-N-methylbenzamide → HCID 58292879, compound

HRID 1948108Notes

Reaction equation

HRID 1948108 reaction equation
NC1C=CC(F)=CC=1C(NC)=O.Cl[C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][N:17]=[C:16]([NH:24][C:25]2[CH:39]=[CH:38][C:28]([CH2:29][P:30](=[O:37])([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33])=[CH:27][C:26]=2[O:40][CH3:41])[N:15]=1.Cl.[CH2:43]([O:45][P:46]([CH2:51][N:52]1[C:61]2[C:56](=[C:57]([NH2:62])[CH:58]=[CH:59][CH:60]=2)[C:55](=[O:63])[C:54]([CH3:64])=[CH:53]1)(=[O:50])[O:47][CH2:48][CH3:49])[CH3:44]>>[CH2:43]([O:45][P:46]([CH2:51][N:52]1[C:61]2[C:56](=[C:57]([NH:62][C:14]3[C:19]([C:20]([F:21])([F:23])[F:22])=[CH:18][N:17]=[C:16]([NH:24][C:25]4[CH:39]=[CH:38][C:28]([CH2:29][P:30]([O:31][CH2:32][CH3:33])([O:34][CH2:35][CH3:36])=[O:37])=[CH:27][C:26]=4[O:40][CH3:41])[N:15]=3)[CH:58]=[CH:59][CH:60]=2)[C:55](=[O:63])[C:54]([CH3:64])=[CH:53]1)(=[O:50])[O:47][CH2:48][CH3:49])[CH3:44]

Participants

4

Reactant 3

HCID 431325582-Amino-5-fluoro-N-methylbenzamideHCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 86654061HCID 86654061, compound2×

Product 1

HCID 58292879HCID 58292879, compound

Procedure

The title compound was prepared according to Compound 102A using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (45.4 mg, 0.100 mmol) and diethyl[(5-amino-3-methyl-4-oxoquinolin-1(4H)-yl)methyl]phosphonate hydrochloride (Compound 303A, 39.7 mg, 0.110 mmol). 1H NMR (CD3OD, 400 MHz): δ=1.24 (t, J=7.2 Hz, 6H), 1.28 (t, J=7.2 Hz, 6H), 2.12 (s, 3H), 3.28 (d, J=21.2 Hz, 2H), 3.91 (s, 3H), 4.06-4.11 (m, 8H), 4.86 (s, 2H), 6.91 (d, J=8.4 Hz, 1H), 7.04 (m, 1H), 7.44 (d, J=8.8 Hz, 1H), 7.62 (m, 1H), 7.92 (s, 1H), 7.96 (dd, J=2.4, 8.4 Hz, 1H), 8.37 (s, 1H), 8.67 (d, J=8.0 Hz, 1H). MS (ES+): m/z 742.18 [MH+]. HPLC: tR=1.44 min (UPLC TOF, polar—3 min).

Workup

  1. customHPLC: tR=1.44 min (UPLC TOF, polar—3 min)

Sources & evidence

ORD record
ord-81489d9e26334e7e98bfd4c85fe58af0
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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