1-Methylpiperazine → [3-Chloro-2-fluoro-5-(4-methyl-piperazine-1-carbonyl)-benzyl]-carbamic acid tert-butyl ester

HRID 1527513Notes

Reaction equation

HRID 1527513 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([Cl:20])[C:18]=1[F:19])[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:45][N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:13]([N:49]2[CH2:50][CH2:51][N:46]([CH3:45])[CH2:47][CH2:48]2)=[O:15])[CH:16]=[C:17]([Cl:20])[C:18]=1[F:19])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 682834143-(Tert-butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid

Product 1

HCID 68284397[3-Chloro-2-fluoro-5-(4-methyl-piperazine-1-carbonyl)-benzyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

was prepared according to Scheme C3 (step A) from 3-(tert-butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid (150 mg, 0.49 mmol), HATU (282 mg, 0.74 mmol), 4-methylpiperazine (59 mg, 0.59 mmol) and DIPEA (0.26 mL, 1.5 mmol) in DMF (2 mL). MS (LC-MS): 386.0 [M]+; tR (HPLC conditions c): 3.77 min.

Workup

  1. customwas prepared
  2. custom3.77 min.

Sources & evidence

ORD record
ord-d2425f510d1a46ee9948a18ab55bab9f
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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