Trifluoroacetic acid → HCID 10413663, compound

HRID 1353483Notes

Reaction equation

CC(O[C:6](=[O:22])[NH:7][C@@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[C:9]1=[O:21])(C)C.C(O)(C(F)(F)F)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+].[Cl:47][C:48]1[CH:57]=[C:56]2[C:51]([C:52]([N:59]3[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]3)=[CH:53][C:54]([NH2:58])=[N:55]2)=[CH:50][CH:49]=1>>[NH2:58][C:54]1[CH:53]=[C:52]([N:59]2[CH2:60][CH2:61][N:62]([C:6]([NH:7][C@H:8]3[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15](=[O:20])[C:16]([CH3:17])([CH3:18])[CH3:19])[C:9]3=[O:21])=[O:22])[CH2:63][CH2:64]2)[C:51]2[C:56](=[CH:57][C:48]([Cl:47])=[CH:49][CH:50]=2)[N:55]=1

Participants

Reactant 5

HCID 6422Trifluoroacetic acid

HCID 94429Triphosgene

HCID 516892Sodium Bicarbonate

HCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamine

HCID 21101828HCID 21101828, compound

Product 1

HCID 10413663HCID 10413663, compound

Procedure

As described for example 213, [(3R)-1-(2,2-dimethyl-1-oxopropyl)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 light yellow solid. LC-MS: 501 (M++1). 1H NMR (CDCl3) δ 1.30 (s, 9H), 1.50˜1.70 (m, 1H), 1.80˜2.08 (m, 3H), 2.10–2.20 (m, 1H), 3.05˜3.20 (m, 4H), 3.45 (dd, 1H), 3.60–3.74 (m, 4H), 3.80 (br.dd, 1H), 4.66 (m, 1H), 4.94 (br.s, 2H), 5.96 (d, 1H), 6.15 (s, 1H), 7.16 (dd, 1H), 7.60 (d, 1H), 7.71 (d, 1H).

Workup

customare reacted

Sources & evidence

ORD record: ord-f3f1900b865f4177b653e4a1bd294bfd
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220856B2

Reaction notes

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