Trifluoroacetic acid → HCID 10322693, compound

HRID 1353485Notes

Reaction equation

HRID 1353485 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]([NH:12][C:13]([O:15]C(C)(C)C)=O)[C:6]1=[O:20])=[O:4].C(O)(C(F)(F)F)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+].[Cl:45][C:46]1[CH:55]=[C:54]2[C:49]([C:50]([N:57]3[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]3)=[CH:51][C:52]([NH2:56])=[N:53]2)=[CH:48][CH:47]=1>>[NH2:56][C:52]1[CH:51]=[C:50]([N:57]2[CH2:58][CH2:59][N:60]([C:13]([NH:12][C@H:7]3[CH2:8][CH2:9][CH2:10][CH2:11][N:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]3=[O:20])=[O:15])[CH2:61][CH2:62]2)[C:49]2[C:54](=[CH:55][C:46]([Cl:45])=[CH:47][CH:48]=2)[N:53]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineHCID 69515101HCID 69515101, compound

Product 1

HCID 10322693HCID 10322693, compound

Procedure

As described for example 213, (3R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]hexahydro-2-oxo-1H-azepine-1-carboxylic acid-methyl ester, TFA, triphosgene, NaHCO3 (sat.), and 7-chloro-4-(1-piperazinyl)-2-quinolinamine are reacted to afford the title product as a light yellow solid. LC-MS: 475 (M++1). 1H NMR (CDCl3): δ 1.45–2.05 (m, 5H), 2.15 (m, 1H), 3.12 (m, 4H), 3.42 (dd, 1H), 3.66 (m, 4H), 3.90 (s, 3H), 4.45 (m, 1H), 4.75˜4.85 (m, 3H), 5.95 (d, 1H), 6.15 (s, 1H), 7.19 (dd, 1H), 7.62 (d, 1H), 7.74 (d, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-8ef4f015fe184e1db5769f84b7086652
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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