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

HRID 1406331노트

반응식

HRID 1406331 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. customThen the mixture was evaporated to dryness

출처 및 근거

ORD 기록
ord-dc8f9206c31b4873a9152464f0952e6f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916589B2

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