Triethylamine → Pyrimidine-5-carboxylic acid-{1-[4-(4-chloro-2-fluoro-phenoxy)-3-fluoro-benzylcarbamoyl]-cyclopropyl}-amide hydrochloride

HRID 1406331Notes

Reaction equation

HRID 1406331 reaction equation
C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:30][C:31]1[CH:46]=[CH:45][C:34]([O:35][C:36]2[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][C:37]=2[F:44])=[C:33]([F:47])[CH:32]=1.[N:48]1[CH:53]=[C:52]([C:54]([NH:56][C:57]2([C:60](O)=[O:61])[CH2:59][CH2:58]2)=[O:55])[CH:51]=[N:50][CH:49]=1>O1CCCC1>[ClH:30].[Cl:30][C:31]1[CH:46]=[CH:45][C:34]([O:35][C:36]2[CH:43]=[CH:42][C:39]([CH2:40][NH:41][C:60]([C:57]3([NH:56][C:54]([C:52]4[CH:51]=[N:50][CH:49]=[N:48][CH:53]=4)=[O:55])[CH2:59][CH2:58]3)=[O:61])=[CH:38][C:37]=2[F:44])=[C:33]([F:47])[CH:32]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584879074-(4-Chloro-2-fluoro-phenoxy)-3-fluoro-benzylamineHCID 594962911-[(Pyrimidine-5-carbonyl)-amino]cyclopropanecarboxylic acid

Product 1

HCID 67447386Pyrimidine-5-carboxylic acid-{1-[4-(4-chloro-2-fluoro-phenoxy)-3-fluoro-benzylcarbamoyl]-cyclopropyl}-amide hydrochlorideYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 mL (3.6 mmol) of triethylamine, 0.433 g (1.35 mmol) of TBTU and 325.5 mg (1.2 mmol) of 4-(4-chloro-2-fluoro-phenoxy)-3-fluoro-benzylamine were added to a solution of 250 mg (1.2 mmol) of 1-[(pyrimidine-5-carbonyl)-amino]-cyclopropanecarboxylic acid (from 1b) in 15 mL tetrahydrofuran and the mixture was stirred overnight at ambient temperature. Then the mixture was evaporated to dryness and the crude product thus obtained was purified by chromatography. The purified product was dissolved in approx. 4 mL ethyl acetate and the dropwise addition of ethereal hydrochloric acid solution caused the hydrochloride to precipitate out, which was then filtered off and dried.

Workup

  1. customThen the mixture was evaporated to dryness

Sources & evidence

ORD record
ord-dc8f9206c31b4873a9152464f0952e6f
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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