HCID 61723431, compound → HCID 59159280, compound

HRID 1096285Notes

Reaction equation

HRID 1096285 reaction equation
IC1C=C(NC(C)C(O)=O)C=CC=1.C([Si](C)(C)O[C@@H]1CN(CCCNCC(OC)OC)CCC21CC2)(C)(C)C.C([Si](C)(C)[O:45][C@@H:46]1[CH2:53][N:52]([CH2:54][CH2:55][CH2:56][N:57]([CH2:70][CH:71](OC)OC)[C:58](=[O:69])[CH:59]([NH:61][C:62]2[CH:67]=[CH:66][CH:65]=[C:64]([I:68])[CH:63]=2)[CH3:60])[CH2:51][CH2:50][C:47]21[CH2:49][CH2:48]2)(C)(C)C.C([Si](C)(C)O[C@@H]1CN(CCCN2CCN(C3C=CC=C(I)C=3)C(C)C2=O)CCC21CC2)(C)(C)C>>[OH:45][C@@H:46]1[CH2:53][N:52]([CH2:54][CH2:55][CH2:56][N:57]2[CH2:70][CH2:71][N:61]([C:62]3[CH:67]=[CH:66][CH:65]=[C:64]([I:68])[CH:63]=3)[CH:59]([CH3:60])[C:58]2=[O:69])[CH2:51][CH2:50][C:47]21[CH2:49][CH2:48]2

Participants

5

Reactant 4

HCID 61723431HCID 61723431, compound2×HCID 66782864HCID 66782864, compoundHCID 66783178HCID 66783178, compoundHCID 66783182HCID 66783182, compound

Product 1

HCID 59159280HCID 59159280, compound

Procedure

The title compound was produced in analogy with examples 87/88, steps A-C. Thus, 2-(3-iodo-phenylamino)-propionic acid (intermediate 23) 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 A, leading to N-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-N-(2,2-dimethoxy-ethyl)-2-(3-iodo-phenylamino)-propionamide. This was cyclized to 1-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-4-(3-iodo-phenyl)-3-methyl-piperazin-2-one in step B. Finally, deprotection in step C afforded the title compound. Light yellow gum, MS: 484.3 (M+H)+)

Sources & evidence

ORD record
ord-7243396caf1e4bd6aef584b4513d25c1
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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