Trifluoroacetic acid → HCID 10007857, compound

HRID 1353489Notes

Reaction equation

HRID 1353489 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]([NH:18][C:19]([O:21]C(C)(C)C)=O)[C:12]2=[O:26])=[O:10])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+].[Cl:51][C:52]1[CH:61]=[C:60]2[C:55]([C:56]([N:63]3[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]3)=[CH:57][C:58]([NH2:62])=[N:59]2)=[CH:54][CH:53]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]([NH:18][C:19]([N:66]3[CH2:67][CH2:68][N:63]([C:56]4[C:55]5[C:60](=[CH:61][C:52]([Cl:51])=[CH:53][CH:54]=5)[N:59]=[C:58]([NH2:62])[CH:57]=4)[CH2:64][CH2:65]3)=[O:21])[C:12]2=[O:26])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineHCID 21101835HCID 21101835, compound

Product 1

HCID 10007857HCID 10007857, compound

Procedure

As described for example 213, (3R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]hexahydro-2-oxo-1H-azepine-1-carboxylic acid-4-fluorophenyl 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: 555 (M++1). 1H NMR (CDCl3): δ 1.54˜2.10 (m, 5H), 2.16–2.24 (m, 1H), 3.14 (m, 4H), 3.54 (dd, 1H), 3.68 (m, 4H), 4.52 (dd, 1H), 4.84 (br.s, 2H), 4.90 (ddd, 1H), 5.94 (d, 1H), 6.15 (s, 1H), 7.06–7.13 (m, 2H), 7.13–7.20 (m, 3H), 7.62 (d, 1H), 7.72 (d, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-6db0a78cd3a34732aaacd0aa45102b1a
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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