Trifluoroacetic acid → 4-(2-Amino-7-chloro-4-quinolinyl)-N-[(3S)-1-(cyclopropylmethyl)hexahydro-2-oxo-1H-azepin-3-yl]-1-piperazinecarboxamide

HRID 1353474Notes

Reaction equation

HRID 1353474 reaction equation
N[C@@H]1CCCCN(CC2CC2)C1=O.[CH:14]1([CH2:17][N:18]2[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]([NH:25][C:26](=[O:32])OC(C)(C)C)[C:19]2=[O:33])[CH2:16][CH2:15]1.C(O)(C(F)(F)F)=O.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.C(N(C(C)C)CC)(C)C.[Cl:63][C:64]1[CH:73]=[C:72]2[C:67]([C:68]([N:75]3[CH2:80][CH2:79][NH:78][CH2:77][CH2:76]3)=[CH:69][C:70]([NH2:74])=[N:71]2)=[CH:66][CH:65]=1>>[NH2:74][C:70]1[CH:69]=[C:68]([N:75]2[CH2:76][CH2:77][N:78]([C:26]([NH:25][C@H:20]3[CH2:21][CH2:22][CH2:23][CH2:24][N:18]([CH2:17][CH:14]4[CH2:15][CH2:16]4)[C:19]3=[O:33])=[O:32])[CH2:79][CH2:80]2)[C:67]2[C:72](=[CH:73][C:64]([Cl:63])=[CH:65][CH:66]=2)[N:71]=1

Participants

7

Reactant 6

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineHCID 57562531(3R)-3-amino-1-(cyclopropylmethyl)hexahydro-2H-azepin-2-oneHCID 86591809[(3S)-1-(cyclopropylmethyl)hexahydro-2-oxo-1H-azepin-3-yl]-carbamic acid, 1,1-dimethylethyl ester

Product 1

HCID 588641644-(2-Amino-7-chloro-4-quinolinyl)-N-[(3S)-1-(cyclopropylmethyl)hexahydro-2-oxo-1H-azepin-3-yl]-1-piperazinecarboxamide

Procedure

As described for example 78, (3R)-3-amino-1-(cyclopropylmethyl)hexahydro-2H-azepin-2-one by de-protection of [(3S)-1-(cyclopropylmethyl)hexahydro-2-oxo-1H-azepin-3-yl]-carbamic acid, 1,1-dimethylethyl ester with TFA, p-nitrophenyl chloroformate, diisopropylethyl amine, and 7-chloro-4-(1-piperazinyl)-2-quinolinamine are reacted to afford the product. LC-MS: 471 (M++1). 1H NMR (CDCl3) δ 7.65 (d, 1H), 7.55 (s, 1H), 7.10 (d, 1H), 6.22 (d, 1H), 6.05 (s, 1H), 4.85 (s, 2H), 4.50 (m, 1H), 3.60 (m, 4H), 3.50 (m, 1H), 3.40 (m, 1H), 3.30 (m, 1H), 3.20 (m, 1H), 3.06 (m, 4H), 2.05 (m, 1H), 1.70–1.90 (m, 3H), 1.40 (m, 2H), 0.90 (m, 1H), 0.45 (m, 2H), 0.20 (m, 2H).

Workup

  1. customare reacted
  2. customto afford the product

Sources & evidence

ORD record
ord-7161566eb67e4dbb94eeb58f5c4b08ed
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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