Trifluoroacetic acid → HCID 10436495, compound

HRID 1353494Notes

Reaction equation

N[C@@H]1CCCCN(C(NC2CCC2)=O)C1=O.CC(O[C:22](=[O:39])[NH:23][C@H:24]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]([C:31]([NH:33][CH:34]2[CH2:37][CH2:36][CH2:35]2)=[O:32])[C:25]1=[O:38])(C)C.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:69][C:70]1[CH:79]=[C:78]2[C:73]([C:74]([N:81]3[CH2:86][CH2:85][NH:84][CH2:83][CH2:82]3)=[CH:75][C:76]([NH2:80])=[N:77]2)=[CH:72][CH:71]=1>>[NH2:80][C:76]1[CH:75]=[C:74]([N:81]2[CH2:82][CH2:83][N:84]([C:22]([NH:23][C@H:24]3[CH2:30][CH2:29][CH2:28][CH2:27][N:26]([C:31]([NH:33][CH:34]4[CH2:35][CH2:36][CH2:37]4)=[O:32])[C:25]3=[O:38])=[O:39])[CH2:85][CH2:86]2)[C:73]2[C:78](=[CH:79][C:70]([Cl:69])=[CH:71][CH:72]=2)[N:77]=1

Participants

Reactant 6

HCID 6422Trifluoroacetic acid

HCID 81531Diisopropylethylamine

HCID 821294-Nitrophenyl chloroformate

HCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamine

HCID 21101902HCID 21101902, compound

HCID 69514565HCID 69514565, compound

Product 1

HCID 10436495HCID 10436495, compound

Procedure

As described example 78, (3R)-3-amino-N-cyclobutylhexahydro-2-oxo-1H-azepine-1-carboxamide by de-protection of [(3S)-1-[(cyclobutylamino)carbonyl]hexahydro-2-oxo-1H-azepin-3-yl] carbamic acid-1,1-dimethylethyl ester with TFA, p-nitrophenyl chloroformate, diisopropyl(ethyl)amine, and 7-chloro-4-(1-piperazinyl)-2-quinolinamine are reacted to afford the product. 1HNMR (DMSO-d6): δ 1.24 (br. s, 1H), 1.5–1.9 (m, 7H), 2.2 (m, 2H), 2.99 (m, 4H), 3.6 (m, 4H), 4.17 (m, 1H), 4.52 (m, 1H), 4.66 (t, 1H), 6.14 (s, 1H, 6.42 (br. s, 1H), 6.8 (d, 1H), 7.1 (d, 1H), 7.39 (s, 1H), 7.76 (d, 1H), 9.3 (d, 1H).

Workup

customare reacted
customto afford the product

Sources & evidence

ORD record: ord-12d13b5ae5f942f99c6a2f6a3e92c079
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220856B2

Reaction notes

Loading…