Triethylamine → Pyrimidine-5-carboxylic acid(1-{1-[4-(4-difluoromethoxy-phenoxy)-phenyl]-ethylcarbamoyl}-cyclopropyl)-amide

HRID 1406367Notes

Reaction equation

HRID 1406367 reaction equation
C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[N:30]1[CH:35]=[C:34]([C:36]([NH:38][C:39]2([C:42]([OH:44])=O)[CH2:41][CH2:40]2)=[O:37])[CH:33]=[N:32][CH:31]=1.[F:45][CH:46]([F:64])[O:47][C:48]1[CH:63]=[CH:62][C:51]([O:52][C:53]2[CH:58]=[CH:57][C:56]([CH:59]([NH2:61])[CH3:60])=[CH:55][CH:54]=2)=[CH:50][CH:49]=1>CN(C=O)C>[F:45][CH:46]([F:64])[O:47][C:48]1[CH:63]=[CH:62][C:51]([O:52][C:53]2[CH:58]=[CH:57][C:56]([CH:59]([NH:61][C:42]([C:39]3([NH:38][C:36]([C:34]4[CH:33]=[N:32][CH:31]=[N:30][CH:35]=4)=[O:37])[CH2:40][CH2:41]3)=[O:44])[CH3:60])=[CH:55][CH:54]=2)=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584879101-[4-(4-Difluoromethoxy-phenoxy)-phenyl]-ethylamineHCID 594962911-[(Pyrimidine-5-carbonyl)-amino]cyclopropanecarboxylic acid

Product 1

HCID 58487824Pyrimidine-5-carboxylic acid(1-{1-[4-(4-difluoromethoxy-phenoxy)-phenyl]-ethylcarbamoyl}-cyclopropyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

376 μL (2.70 mmol) of triethylamine and 0.52 g (1.62 mmol) of TBTU were added to a solution of 0.28 g (1.35 mmol) of 1-[(pyrimidin-5-carbonyl)-amino]-cyclo-propanecarboxylic acid (from 1b) in 5 mL DMF and the mixture was stirred for 5 min at RT. Then 0.42 g (1.50 mmol) of 1-[4-(4-difluoromethoxy-phenoxy)-phenyl]-ethylamine was added and the mixture was stirred for 30 min at ambient temperature. The reaction mixture was purified by chromatography (reversed phase). The acetonitrile was distilled off, the aqueous phase was made basic with ammonia and extracted with dichloromethane. The organic phase was dried and evaporated down.

Workup

  1. stirringthe mixture was stirred for 30 min at ambient temperature
  2. customThe reaction mixture was purified by chromatography (reversed phase)
  3. distillationThe acetonitrile was distilled off
  4. extractionextracted with dichloromethane
  5. customThe organic phase was dried
  6. customevaporated down

Sources & evidence

ORD record
ord-1b7f1da8d8be4e94af0db65b7be0cebc
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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