2-Amino-5-fluoro-N-methylbenzamide → HCID 178472347, compound

HRID 511544Notes

Reaction equation

HRID 511544 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.[NH2:42][C:43]1[CH:52]=[CH:51][C:50]([C@@H:53]2[CH2:58][CH2:57][C@H:56]([C:59]([O:61][CH2:62][CH3:63])=[O:60])[CH2:55][CH2:54]2)=[C:49]2[C:44]=1[C:45](=[O:65])[C:46]([CH3:64])=[CH:47][NH:48]2>>[CH2:32]([O:31][P:30]([CH2:29][C:28]1[CH:38]=[CH:39][C:25]([NH:24][C:16]2[N:15]=[C:14]([NH:42][C:43]3[CH:52]=[CH:51][C:50]([C@@H:53]4[CH2:54][CH2:55][C@H:56]([C:59]([O:61][CH2:62][CH3:63])=[O:60])[CH2:57][CH2:58]4)=[C:49]4[C:44]=3[C:45](=[O:65])[C:46]([CH3:64])=[CH:47][NH:48]4)[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][N:17]=2)=[C:26]([O:40][CH3:41])[CH:27]=1)([O:34][CH2:35][CH3:36])=[O:37])[CH3:33]

Participants

4

Reactant 3

HCID 431325582-Amino-5-fluoro-N-methylbenzamideHCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 178472343HCID 178472343, compound2×

Product 1

HCID 178472347HCID 178472347, 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 (94.83 mg, 0.18 mmol) and ethyl cis-4-(5-amino-3-methyl-4-oxo-1,4-dihydroquinolin-8-yl)cyclohexanecarboxylate (Compound 304B, 70.0 mg, 0.213 mmol). 1H NMR (400 MHz, MeOD) δ ppm 8.57 (br. s., 1H), 8.32 (s, 1H), 7.82-7.88 (m, 2H), 7.48 (d, J=8.6 Hz, 1H), 7.09 (d, J=3.8 Hz, 1H), 6.96 (dt, J=8.1, 2.2 Hz, 1H), 4.16 (q, J=7.2 Hz, 2H), 4.05-4.13 (m, 4H), 3.91 (s, 3H), 3.35 (s, 1H), 3.33 (br. s., 1H), 2.92-3.03 (m, 1H), 2.51 (td, J=11.7, 3.4 Hz, 1H), 2.44-2.56 (m, 1H), 2.17 (br. s., 5H), 1.98 (d, J=10.1 Hz, 2H), 1.63-1.83 (m, 4H), 1.25-1.33 (m, 9H). MS (ES+): m/z:746.20/747.19 (100/40) [MH+]. HPLC: tR=4.44 min (Micromass ZQ3: polar—5 min).

Workup

  1. customHPLC: tR=4.44 min (Micromass ZQ3: polar—5 min)

Sources & evidence

ORD record
ord-307d93cab2d942f1afc6c50e0e725ae3
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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