5-bromo-1H-indazole → HCID 57950621, compound

HRID 598871Notes

Reaction equation

HRID 598871 reaction equation
C(OC([C@@H](CC1C=CC=CC=1)CC(O)=O)=O)(C)(C)C.Cl.N[C@@H](CC1C=CC(C(F)(F)F)=CC=1)CC(O)=O.BrC1C=C2C(=CC=1)NN=C2.N(CC[C@@H](NC(=O)OC(C)(C)C)CC1C=CC=CC=1)=[N+]=[N-].[NH:69]1[C:77]2[C:72](=[CH:73][C:74]([C:78]3[N:79]=[N:80][N:81]([CH2:83][CH2:84][C@@H:85]([NH2:97])[CH2:86][C:87]4[CH:92]=[CH:91][C:90](C(F)(F)F)=[CH:89][CH:88]=4)[CH:82]=3)=[CH:75][CH:76]=2)[CH:71]=[N:70]1>>[NH:69]1[C:77]2[C:72](=[CH:73][C:74]([C:78]3[N:79]=[N:80][N:81]([CH2:83][CH2:84][C@@H:85]([NH2:97])[CH2:86][C:87]4[CH:88]=[CH:89][CH:90]=[CH:91][CH:92]=4)[CH:82]=3)=[CH:75][CH:76]=2)[CH:71]=[N:70]1

Participants

6

Reactant 5

HCID 7619295-bromo-1H-indazoleHCID 2761665(3S)-3-Amino-4-[4-(trifluoromethyl)phenyl]butanoic acid--hydrogen chloride (1/1)HCID 57950500HCID 57950500, compoundHCID 67062694HCID 67062694, compoundHCID 86635696HCID 86635696, compound

Product 1

HCID 57950621HCID 57950621, compound

Procedure

Example 39 was synthesized in a similar fashion as Example 37 as shown in Scheme 12 starting with commercially available (S)-3-(tert-butoxycarbonyl)-4-phenylbutanoic acid (commercially available from PepTech Corporation) instead of (S)-3-amino-4-(4-(trifluoromethyl)phenyl)butanoic acid hydrochloride, and 5-bromo-1H-indazole. The synthesis of the required (S)-tert-butyl 4-azido-1-phenylbutan-2-ylcarbamate was performed in a similar manner as described for the (S)-tert-butyl 4-azido-1-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (Examples 37 and 38) including one additional BOC deprotection step.

Workup

  1. customExample 39 was synthesized in a similar fashion as Example 37

Sources & evidence

ORD record
ord-523ed4a6172a443ea60b2b1a066cd0d0
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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