Trifluoroacetic acid → HCID 11756931, compound

HRID 1353481Notes

Reaction equation

HRID 1353481 reaction equation
[O:1]=[C:2]1[C@@H:8]([NH:9][C:10](=[O:16])OC(C)(C)C)[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:17](=[O:25])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.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>>[NH2:61][C:57]1[CH:56]=[C:55]([N:62]2[CH2:63][CH2:64][N:65]([C:10]([NH:9][C@H:8]3[CH2:7][CH2:6][CH2:5][CH2:4][N:3]([C:17](=[O:25])[CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:2]3=[O:1])=[O:16])[CH2:66][CH2:67]2)[C:54]2[C:59](=[CH:60][C:51]([Cl:50])=[CH:52][CH:53]=2)[N:58]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineHCID 86591811HCID 86591811, compound

Product 1

HCID 11756931HCID 11756931, compound

Procedure

As described for example 213, [(3S)-hexahydro-2-oxo-1-(phenylacetyl)-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: 535 (M++1). 1H NMR (CDCl3, 400 MHz): δ 1.20˜1.50 (m, 2H), 1.80˜2.20 (m, 4H), 3.10˜3.20 (m, 5H), 3.60˜3.70 (m, 4H), 4.28 (AB, 2H), 4.75 (dd, 1H), 4.80˜4.95 (m, 3H), 5.85 (d, 1H), 6.16 (s, 1H), 7.18 (dd, 1H), 7.22˜7.36 (m, 5H), 7.62 (d, 1H), 7.72 (d, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-2f270aa51a194143842fc2f21757fdb5
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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