Triethylamine → Pyrimidine-5-carboxylic acid{1-[4-(4-bromo-2-chloro-phenoxy)-benzylcarbamoyl]-cyclopropyl}-amide

HRID 1406361Notes

Reaction equation

HRID 1406361 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.[Br:45][C:46]1[CH:60]=[CH:59][C:49]([O:50][C:51]2[CH:58]=[CH:57][C:54]([CH2:55][NH2:56])=[CH:53][CH:52]=2)=[C:48]([Cl:61])[CH:47]=1>CN(C=O)C>[Br:45][C:46]1[CH:60]=[CH:59][C:49]([O:50][C:51]2[CH:58]=[CH:57][C:54]([CH2:55][NH:56][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])=[CH:53][CH:52]=2)=[C:48]([Cl:61])[CH:47]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 289663904-(4-Bromo-2-chloro-phenoxy)-benzylamineHCID 594962911-[(Pyrimidine-5-carbonyl)-amino]cyclopropanecarboxylic acid

Product 1

HCID 58487821Pyrimidine-5-carboxylic acid{1-[4-(4-bromo-2-chloro-phenoxy)-benzylcarbamoyl]-cyclopropyl}-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7 μL (0.05 mmol) of triethylamine and 8.4 mg (0.03 mmol) of TBTU were added to a solution of 5.4 mg (0.03 mmol) of 1-[(pyrimidin-5-carbonyl)-amino]-cyclo-propanecarboxylic acid (from 1b) in 1 mL DMF and stirred for 5 min at RT. Then 8 mg (0.03 mmol) of 4-(4-bromo-2-chloro-phenoxy)-benzylamine was added and the mixture was stirred overnight at ambient temperature. The reaction mixture was purified by chromatography (reversed phase).

Workup

  1. stirringthe mixture was stirred overnight at ambient temperature
  2. customThe reaction mixture was purified by chromatography (reversed phase)

Sources & evidence

ORD record
ord-3831e996fe214dc09f18e3f64f0b9e4a
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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