Trifluoroacetic acid → HCID 10433621, compound

HRID 1353482Notes

Reaction equation

HRID 1353482 reaction equation
CC(O[C:6](=[O:18])[NH:7][C@@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH:15]=[O:16])[C:9]1=[O:17])(C)C.C(O)(C(F)(F)F)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+].[Cl:43][C:44]1[CH:53]=[C:52]2[C:47]([C:48]([N:55]3[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]3)=[CH:49][C:50]([NH2:54])=[N:51]2)=[CH:46][CH:45]=1>>[NH2:54][C:50]1[CH:49]=[C:48]([N:55]2[CH2:56][CH2:57][N:58]([C:6]([NH:7][C@H:8]3[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH:15]=[O:16])[C:9]3=[O:17])=[O:18])[CH2:59][CH2:60]2)[C:47]2[C:52](=[CH:53][C:44]([Cl:43])=[CH:45][CH:46]=2)[N:51]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineHCID 21101833HCID 21101833, compound

Product 1

HCID 10433621HCID 10433621, compound

Procedure

As described for example 213, [(3R)-1-formylhexahydro-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 light yellow solid. LC-MS: 445 (M++1). 1H NMR (CDCl3): δ 1.30 (m, 1H), 1.65 (m, 1H), 1.80˜2.30 (m, 4H), 3.09 (dd, 1H), 3.14 (m, 4H), 3.68 (m, 4H), 4.62 (br.dd, 1H), 4.82 (ddd, 1H), 4.90 (br.s, 2H), 5.84 (d, 1H), 6.16 (s, 1H), 7.18 (dd, 1H), 7.62 (d, 1H), 7.72 (d, 1H), 9.47 (s, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-9a971e840ea04059aaf57b92bf887b67
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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