N,N-Dimethylethylenediamine → [3-Chloro-5-(2-dimethylamino-ethylcarbamoyl)-2-fluoro-benzyl]-carbamic acid tert-butyl ester

HRID 1527509Notes

Reaction equation

HRID 1527509 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]([CH3:50])[CH2:47][CH2:48][NH2:49].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](=[O:15])[NH:49][CH2:48][CH2:47][N:46]([CH3:50])[CH3:45])[CH:16]=[C:17]([Cl:20])[C:18]=1[F:19])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 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 68283713[3-Chloro-5-(2-dimethylamino-ethylcarbamoyl)-2-fluoro-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 (116 mg, 0.38 mmol), HATU (218 mg, 0.46 mmol), N,N-dimethylethylenediamine (40 mg, 0.46 mmol) and DIPEA (0.2 mL, 1.1 mmol) in DMF (2 mL). MS (LC-MS): 374.2 [M]+; tR (HPLC conditions c): 3.87 min.

Workup

  1. customwas prepared
  2. custom3.87 min.

Sources & evidence

ORD record
ord-ed2e9416ee8a4ccdb501b42501e6b299
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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