HCID 59471805, compound → HCID 59471950, compound

HRID 2204870Notes

Reaction equation

HRID 2204870 reaction equation
C(S(C1C=CC(C2N=C(C3OC(C4SC(CNC)=CC=4)=NN=3)C(N)=NC=2)=CC=1)(=O)=O)(C)C.C(S(C1C=CC(C2N=C(C3OC(C4SC=C(CNC)C=4)=NN=3)C(N)=NC=2)=CC=1)(=O)=O)(C)C.F[CH:66](F)[CH2:67][NH:68][CH2:69][C:70]1[S:74][C:73]([C:75]2[O:79][C:78]([C:80]3[C:81]([NH2:98])=[N:82][CH:83]=[C:84]([C:86]4[CH:91]=[CH:90][C:89]([S:92]([CH:95]([CH3:97])[CH3:96])(=[O:94])=[O:93])=[CH:88][CH:87]=4)[N:85]=3)=[N:77][N:76]=2)=[CH:72][CH:71]=1.C(NCC1SC(C2OC(C3C(N)=NC=C(C4C=CC(S(C(C)C)(=O)=O)=CC=4)N=3)=NN=2)=CC=1)(C)C>>[CH2:67]([NH:68][CH2:69][C:70]1[S:74][C:73]([C:75]2[O:79][C:78]([C:80]3[C:81]([NH2:98])=[N:82][CH:83]=[C:84]([C:86]4[CH:91]=[CH:90][C:89]([S:92]([CH:95]([CH3:97])[CH3:96])(=[O:94])=[O:93])=[CH:88][CH:87]=4)[N:85]=3)=[N:77][N:76]=2)=[CH:72][CH:71]=1)[CH3:66]

Participants

5

Reactant 4

HCID 59471805HCID 59471805, compoundHCID 59472103HCID 59472103, compoundHCID 59472190HCID 59472190, compoundHCID 59472224HCID 59472224, compound

Product 1

HCID 59471950HCID 59471950, compound

Procedure

Compound IA-140 5-(4-isopropylsulfonylphenyl)-3-[5-[5-(methylaminomethyl)-2-thienyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-amine 1H NMR (400 MHz, DMSO) d 1.22 (d, 6H), 2.65 (s, 3H), 3.42-3.46 (m, 1H), 4.5 (s, 2H), 7.5 (d, 1H), 8.0 (d, 1H), 8.05 (d, 1H), 8.4 (d, 1H), 9.05 (br s, 2H) and 9.1 (s, 1H) ppm; MS (ES+) 471.3 Compound IA-226 5-(4-isopropylsulfonylphenyl)-3-[5-[4-(methylaminomethyl)-2-thienyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-amine 1H NMR (400 MHz, MeOD) d 1.4 (d, 6H), 2.8 (s, 3H), 4.4 (s, 2H), 3.3-3.4 (m, 1H), 8.0-8.1 (m, 3H), 8.12 (s, 1H), 8.35 (d, 2H) and 9.0 (s, 1H) ppm; MS (ES+) 471.3 Compound IA-236 3-[5-[5-[(2,2-difluoroethylamino)methyl]-2-thienyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine 1H NMR (400 MHz, DMSO) d 1.25 (d, 6H), 3.4-3.6 (m, 3H), 4.55 (s, 2H), 6.2-6.5 (m, 1H), 7.5 (d, 1H), 7.8-8.1 (m, 4H), 8.45 (d, 2H) and 9.1 (s, 1H) ppm; MS (ES+) 521.3 Compound IA-248 3-[5-[5-[(isopropylamino)methyl]-2-thienyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine 1H NMR (400 MHz, DMSO) d 1.25 (m, 6H), 1.35 (d, 6H), 3.4-3.6 (m, 2H), 4.6 (s, 2H), 7.5 (d, 1H), 7.95-8.1 (m, 4H), 8.45 (d, 2H), 8.9-9.0 (br s, 2H) and 9.1 (s, 1H) ppm; MS (ES+) 499.4

Sources & evidence

ORD record
ord-b875cc205cf94c059ffcf6e58999f2b8
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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