Trifluoroacetic acid → HCID 10482483, compound

HRID 1353487Notes

Reaction equation

CC(C)(O[C:5]([NH:7][C@@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[O:16])[C:9]1=[O:23])=[O:6])C.C(O)(C(F)(F)F)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+].[Cl:49][C:50]1[CH:59]=[C:58]2[C:53]([C:54]([N:61]3[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]3)=[CH:55][C:56]([NH2:60])=[N:57]2)=[CH:52][CH:51]=1>>[NH2:60][C:56]1[CH:55]=[C:54]([N:61]2[CH2:62][CH2:63][N:64]([C:5]([NH:7][C@H:8]3[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15]([O:17][CH2:18][C:19]([F:20])([F:21])[F:22])=[O:16])[C:9]3=[O:23])=[O:6])[CH2:65][CH2:66]2)[C:53]2[C:58](=[CH:59][C:50]([Cl:49])=[CH:51][CH:52]=2)[N:57]=1

Participants

Reactant 5

HCID 6422Trifluoroacetic acid

HCID 94429Triphosgene

HCID 516892Sodium Bicarbonate

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

HCID 86591812HCID 86591812, compound

Product 1

HCID 10482483HCID 10482483, compound

Procedure

As described for example 213, (3R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]hexahydro-2-oxo-1H-azepine-1-carboxylic acid, 2,2,2-trifluoroethyl 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: 543 (M++1). 1H NMR (DMSO+TFA): δ 1.32–1.45 (m, 1H), 1.56˜1.90 (m, 5H), 3.26 (m, 4H), 3.54–3.66 (m, 5H), 4.15 (m, 1H), 4.68 (br.d, 1H), 4.83 (m, 2H), 6.32 (s, 1H), 7.42 (dd, 1H), 7.60 (d, 1H), 7.90 (d, 1H).

Workup

customare reacted

Sources & evidence

ORD record: ord-b910c8ecdf594fe386b52e779fdb71df
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220856B2

Reaction notes

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