Trifluoroacetic acid → HCID 58864158, compound

HRID 1353491Notes

Reaction equation

HRID 1353491 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][C:21]([F:24])([F:23])[F: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: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:10]([NH:9][C@H:8]3[CH2:7][CH2:6][CH2:5][CH2:4][N:3]([C:17]([NH:19][CH2:20][C:21]([F:22])([F:23])[F:24])=[O:18])[C:2]3=[O:1])=[O:16])[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

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineHCID 86591814HCID 86591814, compound

Product 1

HCID 58864158HCID 58864158, compound

Procedure

As described for example 213, [(3R)-hexahydro-2-oxo-1-[[(2,2,2-trifluoroethyl)amino]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 light yellow solid. LC-MS: 542 (M++1). 1H NMR (CDCl3,): δ 1.44 (m, 1H), 1.64 (m, 1H), 1.82˜2.02 (m, 4H), 3.14 (m, 4H), 3.31 (dd, 1H), 3.68 (m, 4H), 3.98 (m, 2H), 4.84 (dd, 1H), 4.88–5.00 (m, 3H), 5.80 (d, 1H), 6.03 (s, 1H), 7.16 (dd, 1H), 7.60 (d, 1H), 7.71 (d, 1H), 9.54 (t, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-47410645c2c24a78983a66835d037931
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

Loading…