1,2-Ethanediamine, N1,N1,N2-trimethyl- → {3-Chloro-5-[(2-dimethylamino-ethyl)-methyl-amino]-2-fluoro-benzyl}-carbamic acid tert-butyl ester

HRID 1527478Notes

Reaction equation

HRID 1527478 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13](Br)[CH:12]=[C:11]([Cl:16])[C:10]=1[F:17])([CH3:4])([CH3:3])[CH3:2].[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][NH:23][CH3:24].CC(C)([O-])C.[Na+]>>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([N:23]([CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])[CH3:24])[CH:12]=[C:11]([Cl:16])[C:10]=1[F:17])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 23676156Sodium t-butoxideHCID 68283623Carbamic acid, N-[(5-bromo-3-chloro-2-fluorophenyl)methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 68283334{3-Chloro-5-[(2-dimethylamino-ethyl)-methyl-amino]-2-fluoro-benzyl}-carbamic acid tert-butyl ester

Procedure

was prepared according to Scheme C1 (step A) from (5-bromo-3-chloro-2-fluoro-benzyl)-carbamic acid tert-butyl ester (300 mg, 0.89 mmol), N,N,N′-trimethyl-ethylenediamine (136 mg, 1.3 mmol), sodium tert-butoxide (170 mg, 1.8 mmol) and di-μ-bromobis(tri-tert-butylphosphino)dipalladium (I) [CAS 185812-86-6] (34 mg, 0.04 mmol). MS (LC-MS): 360.3 [M]+; tR (HPLC conditions c): 4.15 min.

Workup

  1. customwas prepared
  2. custom4.15 min.

Sources & evidence

ORD record
ord-24fed91ddfd44a2ab08bd84a38281e64
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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