HCID 66782717, compound → HCID 59159316, compound

HRID 1096283Notes

Reaction equation

ClC1C=CC(N[C@@H](C)C(O)=O)=CC=1OC(F)(F)F.C([Si](C)(C)O[C@@H]1CN(CCCNCC(OC)OC)CCC21CC2)(C)(C)C.C([Si](C)(C)[O:50][C@@H:51]1[CH2:58][N:57]([CH2:59][CH2:60][CH2:61][N:62]([CH2:80][CH:81](OC)OC)[C:63](=[O:79])[C@@H:64]([NH:66][C:67]2[CH:72]=[CH:71][C:70]([Cl:73])=[C:69]([O:74][C:75]([F:78])([F:77])[F:76])[CH:68]=2)[CH3:65])[CH2:56][CH2:55][C:52]21[CH2:54][CH2:53]2)(C)(C)C.C([Si](C)(C)O[C@@H]1CN(CCCN2CCN(C3C=CC(Cl)=C(OC(F)(F)F)C=3)[C@@H](C)C2=O)CCC21CC2)(C)(C)C>>[Cl:73][C:70]1[CH:71]=[CH:72][C:67]([N:66]2[CH2:81][CH2:80][N:62]([CH2:61][CH2:60][CH2:59][N:57]3[CH2:56][CH2:55][C:52]4([CH2:53][CH2:54]4)[C@H:51]([OH:50])[CH2:58]3)[C:63](=[O:79])[C@@H:64]2[CH3:65])=[CH:68][C:69]=1[O:74][C:75]([F:77])([F:76])[F:78]

Participants

Reactant 4

HCID 66782717HCID 66782717, compound2×

HCID 66782864HCID 66782864, compound

HCID 66783733HCID 66783733, compound

HCID 66783735HCID 66783735, compound

Product 1

HCID 59159316HCID 59159316, compound

Procedure

The title compound was produced in analogy with example 83, steps D-F. Thus, (S)-2-(4-chloro-3-trifluoromethoxy-phenylamino)-propionic acid (intermediate 19) was coupled with {3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-(2,2-dimethoxy-ethyl)-amine (example 83C) in step D, leading to (S)—N-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-2-(4-chloro-3-trifluoromethoxy-phenylamino)-N-(2,2-dimethoxy-ethyl)-propionamide. This was cyclized to (S)-1-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-4-(4-chloro-3-trifluoromethoxy-phenyl)-3-methyl-piperazin-2-one in step E. Finally, deprotection in step F afforded the title compound. Light yellow gum, MS: 476.2 (M+H)+.

Sources & evidence

ORD record: ord-d62b7cc607f14347b2bbfe9a918d6eed
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138175B2

Reaction notes

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