Trifluoroacetic acid → HCID 10480006, compound

HRID 1353495Notes

Reaction equation

HRID 1353495 reaction equation
CC(O[C:6](=[O:20])[NH:7][C@@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15]([NH:17][CH3:18])=[O:16])[C:9]1=[O:19])(C)C.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:6]([NH:7][C@H:8]3[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15]([NH:17][CH3:18])=[O:16])[C:9]3=[O:19])=[O:20])[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 21101880HCID 21101880, compound

Product 1

HCID 10480006HCID 10480006, compound

Procedure

As described for example 213, [(3R)-Hexahydro-1-[(methylamino)carbonyl]-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 powder. LC-MS, 473 (M+). 1H NMR (400 MHz, DMSO): 61.38 (m, 1H), 1.57 (m, 1H), 1.9 (m, 2H), 2.03 (br. d, 1H), 2.19 (s, 1H), 2.85 (d, 3H), 3.08 (m, 4H), 3.21 (m, 1H), 3.63 (m, 4H), 4.83 (m, 1H), 4.85 (m, 1H), 4.95 (s, 2H), 5.85 (d, 1H), 6.11 (s, 1H), 7.11 (dd, 1H), 7.56 (d, 1H), 7.67 (d, 1H), 8.91 (q, 1).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-c26098f9c08b4288aa1f35c01aee8d92
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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