Trifluoroacetic acid → HCID 10368750, compound

HRID 1353493Notes

Reaction equation

HRID 1353493 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]([NH:19][CH2:20][CH2:21][CH3:22])=[O:18].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:10]([NH:9][C@H:8]3[CH2:7][CH2:6][CH2:5][CH2:4][N:3]([C:17]([NH:19][CH2:20][CH2:21][CH3:22])=[O:18])[C:2]3=[O:1])=[O:16])[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

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineHCID 86591815HCID 86591815, compound

Product 1

HCID 10368750HCID 10368750, compound

Procedure

As described for example 213, [(3R)-hexahydro-2-oxo-1-[(propylamino)carbonyl]-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 white solid. LC-MS: 502 (M++1). 1H NMR (CD3OD) δ 0.95 (t, 3H), 1.55 (m, 4H), 1.90 (m, 3H), 2.10 (d, 1H), 3.10 (m, 4H), 3.25 (m, 3H), 3.65 (m, 4H), 4.80–4.95 (m, 4H), 5.86 (d, 1H), 6.12 (s, 1H), 7.12 (d, 1H), 7.58 (s, 1H), 7.65 (d, 1H), 9.00 (m, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-d19680197b0246be99ae0f7f7d9ff8cf
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

Loading…