Trifluoroacetic acid → HCID 10389500, compound

HRID 1353490Notes

Reaction equation

HRID 1353490 reaction equation
CC(O[C:6](=[O:19])[NH:7][C@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15]([NH2:17])=[O:16])[C:9]1=[O:18])(C)C.C(O)(C(F)(F)F)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+].[Cl:44][C:45]1[CH:54]=[C:53]2[C:48]([C:49]([N:56]3[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]3)=[CH:50][C:51]([NH2:55])=[N:52]2)=[CH:47][CH:46]=1>>[NH2:55][C:51]1[CH:50]=[C:49]([N:56]2[CH2:57][CH2:58][N:59]([C:6]([NH:7][C@H:8]3[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15]([NH2:17])=[O:16])[C:9]3=[O:18])=[O:19])[CH2:60][CH2:61]2)[C:48]2[C:53](=[CH:54][C:45]([Cl:44])=[CH:46][CH:47]=2)[N:52]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineHCID 21101898HCID 21101898, compound

Product 1

HCID 10389500HCID 10389500, compound

Procedure

As described for example 213, [(3S)-1-(aminocarbonyl)hexahydro-2-oxo-1H-azepin-3-yl]-carbamic acid-1,1-dimethylethyl ester, TFA, triphosgene, NaHCO3 (sat.), and 7-chloro-4-(1-piperazinyl)-2-quinolinamine are reacted to afford the product as a white solid. LC-MS: 460 (M++1). 1H NMR (DMSO-d6+TFA): 1.16˜1.30 (m, 1H), 1.54˜1.88 (m, 5H), 3.26 (m, 4H), 3.60 (m, 4H), 4.56 (ddd, 1H), 4.70 (br.dd, 1H), 6.32 (s, 1H), 7.38–7.46 (m, 2H), 7.62 (d, 1H), 7.88 (d, 1H), 8.20–8.50 (m, 3H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-c83e0d640a99486184decd09fdf91672
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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