Trifluoroacetic acid → HCID 10052910, compound

HRID 1353488Notes

Reaction equation

HRID 1353488 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][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])[C:9]1=[O:24])=[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:50][C:51]1[CH:60]=[C:59]2[C:54]([C:55]([N:62]3[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]3)=[CH:56][C:57]([NH2:61])=[N:58]2)=[CH:53][CH:52]=1>>[C:18]1([O:17][C:15]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C@H:8]([NH:7][C:5]([N:65]3[CH2:66][CH2:67][N:62]([C:55]4[C:54]5[C:59](=[CH:60][C:51]([Cl:50])=[CH:52][CH:53]=5)[N:58]=[C:57]([NH2:61])[CH:56]=4)[CH2:63][CH2:64]3)=[O:6])[C:9]2=[O:24])=[O:16])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineHCID 86591813HCID 86591813, compound

Product 1

HCID 10052910HCID 10052910, compound

Procedure

As described for example 213, (3R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]hexahydro-2-oxo-1H-azepine-1-carboxylic acid, phenyl 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: 537 (M++1). 1H NMR (CDCl3,) δ 1.56˜2.08 (m, 5H), 2.16–2.24 (m, 1H), 3.14 (m, 4H), 3.54 (dd, 1H), 3.68 (m, 4H), 4.54 (br.dd, 1H), 4.84 (br.s, 2H), 4.90 (ddd, 1H), 5.80 (d, 1H), 6.15 (s, 1H), 7.16˜7.22 (m, 3H), 7.27 (m, 1H), 7.41 (m, 2H), 7.62 (d, 1H), 7.72 (d, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-29cb56097642476ca853724774203493
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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