Diisopropylethylamine → HCID 71290299, compound

HRID 536504Notes

Reaction equation

HRID 536504 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]=[C:13](I)[C:14]4[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[NH:17][C:15]=4[N:16]=3)=[N:9][N:8]([CH2:24][C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][N:26]=3)[C:5]2=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C.Cl.[F:42][CH:43]1[CH2:46][NH:45][CH2:44]1>CN1CCCC1=O>[F:42][CH:43]1[CH2:46][N:45]([C:13]2[C:14]3[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[NH:17][C:15]=3[N:16]=[C:11]([C:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([F:1])[CH:3]=4)[N:8]([CH2:24][C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][N:26]=4)[N:9]=3)[N:12]=2)[CH2:44]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 101250543-fluoroazetidine HydrochlorideHCID 71503129HCID 71503129, compound

Product 1

HCID 71290299HCID 71290299, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

150 mg (0.155 mmol, approx. 55% purity) of the compound obtained in example 21A was dissolved in 1-methyl-2-pyrrolidone (2.7 ml) in a reaction vessel suitable for a microwave, and 0.423 ml (2.430 mmol) of N,N-diisopropyl ethylamine and 270 mg (2.420 mmol) of 3-fluoroazetidine hydrochloride were added. Then it was sealed with a corresponding septum and it was heated in the microwave at 150° C. for 3 h. After cooling, the reaction mixture was purified by preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). 30 mg of the title compound was obtained (40% of theor.).

Workup

  1. additionwere added
  2. customThen it was sealed with a corresponding septum and it
  3. temperatureAfter cooling
  4. customthe reaction mixture was purified by preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-fd30bb99efdd4e0fb76f03a03d387fa6
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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