Trifluoroacetic acid → HCID 178491965, compound

HRID 591946Notes

Reaction equation

HRID 591946 reaction equation
FC(F)(F)C(O)=O.ClC1C(N[C@@H]2[C@@H]3C[C@@H](C=C3)[C@@H]2C(N)=O)=C2N=C(C3C=CC(CN4CCOCC4)=CC=3)NC2=NC=1.[NH2:42][C:43]1[C:48]([NH2:49])=[C:47]([NH:50][C@@H:51]2[C@@H:56]3[CH2:57][C@@H:53]([CH:54]=[CH:55]3)[C@@H:52]2[C:58]([NH2:60])=[O:59])[C:46]([Cl:61])=[CH:45][N:44]=1.C(OC([N:69]1[CH2:74][CH2:73][N:72]([CH2:75][C:76]2[CH:81]=[CH:80][C:79]([CH:82]=O)=[C:78]([O:84][CH3:85])[CH:77]=2)[CH2:71][CH2:70]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[Cl:61][C:46]1[C:47]([NH:50][C@@H:51]2[C@@H:56]3[CH2:57][C@@H:53]([CH:54]=[CH:55]3)[C@@H:52]2[C:58]([NH2:60])=[O:59])=[C:48]2[N:49]=[C:82]([C:79]3[CH:80]=[CH:81][C:76]([CH2:75][N:72]4[CH2:73][CH2:74][NH:69][CH2:70][CH2:71]4)=[CH:77][C:78]=3[O:84][CH3:85])[NH:42][C:43]2=[N:44][CH:45]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 89725669HCID 89725669, compoundHCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideHCID 178513995HCID 178513995, compound

Product 1

HCID 178491965HCID 178491965, compoundYield 10%

Procedure

In the same fashion as for Compound III, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide and 4-(4-formyl-3-methoxy-benzyl)-piperazine-1-carboxylic acid tert-butyl ester were reacted to produce a material which following treatment with trifluoroacetic acid at 40° C. for four hours, followed by concentration and neutralization afforded the title compound (10%). 1H NMR (d-4 methanol): 8.30 (d, J=7 Hz, 1H), 8.11 (s, 1H), 7.40 (s, 1H), 7.27 (d, J=7 Hz, 1H), 6.47 (m, 2H), 5.09 (m, 1H), 4.34 (m, 2H), 4.13 (s, 3H), 3.73 (s, 1H), 3.56 (s, 4H), 3.44 (s, 4H), 3.07 (s 1H), 3.02 (s, 1H), 2.75 (s, J=8 Hz, 1H), 2.18 (m, 2H), 1.87 (s, 1H), 1.58 (d, J=8 Hz, 1H), 1.30 (s, 1H). MS: 508.2 (M+H). HPLC retention time: 1.66 minutes (G Method).

Workup

  1. customto produce a material which
  2. customat 40° C.
  3. customfor four hours
  4. concentrationfollowed by concentration and neutralization

Sources & evidence

ORD record
ord-4ebf996796b24b5ba9504237360de698
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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