4-Methylmorpholine → 2-(3-((7-(3-chloropropoxy)quinazolin-4-yl)amino)-1H-pyrazol-5-yl)-N-(3-fluorophenyl)acetamide

HRID 1864479노트

반응식

HRID 1864479 반응식
CN1CCOCC1.[F:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].Cl.[Cl:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[C:30]2[C:25]([C:26]([NH:32][C:33]3[CH:37]=[C:36]([CH2:38][C:39](O)=[O:40])[NH:35][N:34]=3)=[N:27][CH:28]=[N:29]2)=[CH:24][CH:23]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.CN(C)C(=O)C.O.C(#N)C>[Cl:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[C:30]2[C:25]([C:26]([NH:32][C:33]3[CH:37]=[C:36]([CH2:38][C:39]([NH:12][C:11]4[CH:13]=[CH:14][CH:15]=[C:9]([F:8])[CH:10]=4)=[O:40])[NH:35][N:34]=3)=[N:27][CH:28]=[N:29]2)=[CH:24][CH:23]=1

참가 물질

9

반응물 4

HCID 79724-MethylmorpholineHCID 97423-FluoroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67000008(3-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-5-yl)acetic acid hydrochloride

생성물 1

HCID 162214542-(3-((7-(3-chloropropoxy)quinazolin-4-yl)amino)-1H-pyrazol-5-yl)-N-(3-fluorophenyl)acetamide

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매2회HCID 6342Acetonitrile용매HCID 31374Dimethylacetamide용매

실험 절차

4-Dimethylaminopyridine (DMAP), N-methylmorpholine and 3-fluoroaniline (in a large excess) were added to a suspension of (3-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-5-yl)acetic acid.hydrochloride in N,N-dimethylacetamide (DMA) and the resulting slurry was stirred at or below room temperature. A solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI.HCl) previously dissolved in water was then added in a controlled manner over a period of 8 hour so as to maintain the reaction at ambient temperature. The mixture was seeded with a small amount of product and left to stir for several hours. Anti-solvent acetonitrile followed by water were also added to precipitate more product. The material was isolated by filtration and the cake washed with a mixture of N,N-dimethylacetamide:water:acetonitrile, warm acetonitrile and then dried (in vacuo or under a stream of nitrogen) to yield 2-(3-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-5-yl)-N-(3-fluorophenyl)acetamide.

후처리

  1. additionwas then added in a controlled manner over a period of 8 hour so as
  2. temperatureto maintain
  3. customthe reaction at ambient temperature
  4. waitleft
  5. stirringto stir for several hours
  6. additionwere also added
  7. customto precipitate more product
  8. customThe material was isolated by filtration
  9. washthe cake washed with a mixture of N,N-dimethylacetamide
  10. temperaturewater:acetonitrile, warm acetonitrile
  11. customdried (in vacuo

출처 및 근거

ORD 기록
ord-3ec6c6d8208c404b9b61880d1c0b3b5b
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625910B2

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