Trifluoroacetic acid → 4-[(4-tert-Butylpiperazin-2-yl)carbonyl]-N-(3,4-dichlorophenyl)piperazine-1-carboxamide

HRID 603261Notes

Reaction equation

HRID 603261 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH:9]1[C:18]([OH:20])=O)=O)(C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(O)(C(F)(F)F)=O.[Cl:52][C:53]1[CH:54]=[C:55]([NH:60][C:61]([N:63]2[CH2:68][CH2:67][N:66](C([C@H]3CN(C(C)C)CCN3)=O)[CH2:65][CH2:64]2)=[O:62])[CH:56]=[CH:57][C:58]=1[Cl:59]>>[C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH:9]([C:18]([N:66]2[CH2:65][CH2:64][N:63]([C:61]([NH:60][C:55]3[CH:56]=[CH:57][C:58]([Cl:59])=[C:53]([Cl:52])[CH:54]=3)=[O:62])[CH2:68][CH2:67]2)=[O:20])[CH2:10]1)([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534031224-tert-Butyl-piperazine-1,2-dicarboxylic acid 1-tert-butyl esterHCID 57656833N-(3,4-Dichlorophenyl)-4-{[(2R)-4-isopropylpiperazin-2-yl]carbonyl}piperazine-1-carboxamide

Product 1

HCID 576568794-[(4-tert-Butylpiperazin-2-yl)carbonyl]-N-(3,4-dichlorophenyl)piperazine-1-carboxamide

Procedure

4-[(4-tert-Butylpiperazin-2-yl)carbonyl]-N-(3,4-dichlorophenyl)piperazine-1-carboxamide was prepared from 1-(tert-butoxycarbonyl)-4-tert-butylpiperazine-2-carboxylic acid using an identical HATU coupling TFA deprotection sequence as previously described for N-(3,4-dichlorophenyl)-4-{[(2R)-4-isopropylpiperazin-2-yl]carbonyl}piperazine-1-carboxamide (Route E1).

Sources & evidence

ORD record
ord-1bf374bc9db64717934e7837a7c15015
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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