HCID 66745300, compound → HCID 66745527, compound

HRID 1959462Notes

Reaction equation

HRID 1959462 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]([C:26]2[O:30][C:29]([C:31]3[CH:36]=[CH:35][C:34]([CH2:37][N:38](C)[C:39](=O)OC(C)(C)C)=[CH:33][CH:32]=3)=[N:28][N:27]=2)=[N:11][C:12]([N:15]2[CH2:20][C@H:19]3[C@H:17]([CH:18]3[C:21](=[O:25])[N:22]([CH3:24])[CH3:23])[CH2:16]2)=[CH:13][N:14]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[CH2:20][C@H:19]3[C@H:17]([CH:18]3[C:21]([N:22]([CH3:23])[CH3:24])=[O:25])[CH2:16]2)=[N:11][C:10]=1[C:26]1[O:30][C:29]([C:31]2[CH:32]=[CH:33][C:34]([CH2:37][NH:38][CH3:39])=[CH:35][CH:36]=2)=[N:28][N:27]=1

Participants

3

Reactant 1

HCID 66745300HCID 66745300, compound

Product 1

HCID 66745527HCID 66745527, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-[(1R,5S)-6-(dimethylcarbamoyl)-3-azabicyclo[3.1.0]hexan-3-yl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (75 mg, 0.1 mmol) in 0.8 mL of 50% TFA-DCM mixture was stirred under an atmosphere of nitrogen at room temperature for 1 h. The solvents were evaporated and the crude material was purified via reverse phase HPLC using 10 to 99% methanol in water (TFA modifier) to obtain (1R,5S)-3-[5-amino-6-[5-[4-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-3-azabicyclo[3.1.0]hexane-6-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ 8.87 (s, 2H), 8.16 (d, J=8.2 Hz, 2H), 7.91 (s, 1H), 7.73 (d, J=8.2 Hz, 2H), 6.76 (s, 2H), 4.26 (t, J=5.7 Hz, 2H), 3.86 (d, J=10.2 Hz, 2H), 3.49-3.46 (m, 2H), 3.10 (s, 3H), 2.84 (s, 3H), 2.63 (t, J=5.2 Hz, 3H), 2.09 (s, 2H), 1.90 (t, J=3.1 Hz, 1H). LC/MS m/z 435.2 [M+H]+.

Workup

  1. customThe solvents were evaporated
  2. customthe crude material was purified via reverse phase

Sources & evidence

ORD record
ord-354ec6a32880416f8c56821432fafeab
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

Loading…