Trifluoroacetic acid → HCID 9983235, compound

HRID 1353484Notes

Reaction equation

HRID 1353484 reaction equation
CC(O[C:6](=[O:20])[NH:7][C@@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([S:15]([CH3:18])(=[O:17])=[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]([S:15]([CH3:18])(=[O:16])=[O:17])[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 21101881HCID 21101881, compound

Product 1

HCID 9983235HCID 9983235, compound

Procedure

As described for example 213, [(3R)-hexahydro-1-(methylsulfonyl)-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: 495 (M++1). 1H NMR (CDCl3) δ 1.52 (m, 1H), 1.70 (m, 1H), 1.86 (m, 1H), 1.95˜2.05 (m, 2H), 2.15 (m, 1H), 3.09 (m, 4H), 3.45 (s, 3H), 3.48 (m, 1H), 3.65 (m, 4H), 4.45 (m, 1H), 4.81 (m, 1H), 5.17 (br.s, 2H), 5.95 (d, 1H), 6.15 (s, 1H), 7.15 (dd, 1H), 7.60 (d, 1H), 7.69 (d, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-79405c2b0e4f40828a895cdaf79ffe84
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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