Trifluoroacetic acid → HCID 9982977, compound

HRID 1353486Notes

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][CH3:19])=[O:16])[C:9]1=[O:20])=[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:46][C:47]1[CH:56]=[C:55]2[C:50]([C:51]([N:58]3[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]3)=[CH:52][C:53]([NH2:57])=[N:54]2)=[CH:49][CH:48]=1>>[CH2:18]([O:17][C:15]([N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@H:8]([NH:7][C:5]([N:61]2[CH2:62][CH2:63][N:58]([C:51]3[C:50]4[C:55](=[CH:56][C:47]([Cl:46])=[CH:48][CH:49]=4)[N:54]=[C:53]([NH2:57])[CH:52]=3)[CH2:59][CH2:60]2)=[O:6])[C:9]1=[O:20])=[O:16])[CH3:19]

Participants

Reactant 5

HCID 6422Trifluoroacetic acid

HCID 94429Triphosgene

HCID 516892Sodium Bicarbonate

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

HCID 69514697HCID 69514697, compound

Product 1

HCID 9982977HCID 9982977, compound

Procedure

As described for example 213, (3R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]hexahydro-2-oxo-1H-azepine-1-carboxylic acid, ethyl ester, TFA, triphosgene, NaHCO3 (sat.), and 7-chloro-4-(1-piperazinyl)-2-quinolinamine are reacted to afford the title product as a light yellow solid. LC-MS: 489 (M++1). 1H NMR (CDCl3): δ 1.37 (t, 3H), 1.44˜2.02 (m, 5H), 2.12˜2.20 (m, 1H), 3.13 (m, 4H), 3.41 (dd, 1H), 3.67 (m, 4H), 4.35 (m, 2H), 4.42 (m, 1H), 4.74˜4.86 (m, 3H), 6.00 (d, 1H), 6.16 (s, 1H), 7.18 (dd, 1H), 7.62 (d, 1H), 7.73 (d, 1H).

Workup

customare reacted

Sources & evidence

ORD record: ord-3cd5c832db694ff68d21f4d54a511356
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220856B2

Reaction notes

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