Dimethylamine → (3-Chloro-5-dimethylcarbamoyl-2-fluoro-benzyl)-carbamic acid tert-butyl ester

HRID 1527502Notes

Reaction equation

HRID 1527502 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](O)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][N:22](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:23].F[P-](F)(F)(F)(F)F.CNC.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:14])[N:22]([CH3:23])[CH3:21])[CH:16]=[C:17]([Cl:20])[C:18]=1[F:19])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 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 68284266(3-Chloro-5-dimethylcarbamoyl-2-fluoro-benzyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(tert-butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid (100 mg, 0.3 mmol), HATU (188 mg, 0.5 mmol), dimethylamine (0.2 mL, 2M in THF) and DIPEA (0.23 mL, 1.3 mmol) in DMF (2 mL) was stirred for 16 h at ambient temperature. The crude product was purified without aqueous workup by RP-preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 ml/min) to give the title compound. MS (LC-MS): 275.0 [M−55]+; tR (HPLC conditions c): 4.68 min.

Workup

  1. customThe crude product was purified without aqueous workup by RP-preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 ml/min)

Sources & evidence

ORD record
ord-0bdbf32accd644c4ab078db774102063
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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