4-Quinolinecarboxylic acid → HCID 11191627, 화합물

HRID 393421

반응식

HRID 393421 반응식
C[O:2][C:3](=[O:28])[C@H:4]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)[NH:5][C:6]([C:8]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([C:39]([OH:41])=O)=[CH:31][CH:30]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[OH-].[Na+]>CN(C=O)C.C(OCC)(=O)C.CCOCC.CO>[C:14]1([CH2:13][C:8]2([C:6]([NH:5][C@H:4]([C:3]([OH:28])=[O:2])[CH2:20][C:21]3[CH:22]=[CH:23][C:24]([NH:27][C:39]([C:32]4[C:33]5[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=5)[N:29]=[CH:30][CH:31]=4)=[O:41])=[CH:25][CH:26]=3)=[O:7])[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

10

반응물 5

HCID 102434-Quinolinecarboxylic acidHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53841867HCID 53841867, 화합물

생성물 1

HCID 11191627HCID 11191627, 화합물

시약·촉매·용매 4

HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-amino-N-[[1-(phenylmethyl)cyclopentyl]carbonyl]-L-phenylalanine methyl ester (29.5 mg, 0.078 mmol), quinoline-4-carboxylic acid (17 mg, 0.10 mmol), and HBTU (38 mg, 0.10 mmol) in 1 mL of DMF was treated with diisopropylethylamine (30 μL, 0.17 mmol). The mixture was stirred over night and was diluted with 15 mL of ethyl acetate and 10 mL of ether and was washed with portions of water (2×10 mL), saturated NaHCO3 (10 mL) and was dried (MgSO4). Concentration gave 48 mg which was dissolved in 3 mL of methanol. Sodium hydroxide solution (0.10 mL, 4 N, 0.4 mmol) was added and the mixture was stirred for 2 hr. The excess base was quenched by addition of 0.1 mL of acetic acid, the solution was filtered through a 0.2μ nylon filter and the filtrate was purified by RP-HPLC on a 4×30 cm Rainin C-18 column using a gradient of 5 to 95% acetonitrile:water containing 0.75% trifluoroacetic acid at a flow of 49 mL/min over 30 min. The peak eluting at 74.5% acetonitrile was the acid N-[[1-(phenylmethyl)cyclopentyl]carbonyl]-4-[(4-quinolinylcarbonyl)amino)-L-phenylalanine (15 mg), HR—FAB—MS: obs. mass 522.2393. Calcd. mass 522.2393 (M+H), the peak eluting at 83% acetonitrile was recovered N-[[1-(phenylmethyl)cyclopentyl]carbonyl]-4-[(4-quinolinylcarbonyl)amino]-L-phenylalanine methyl ester (15 mg), HR—FAB—MS: obs. mass 536.2556. Calcd. mass 536.2549 (M+H).

후처리

  1. washwas washed with portions of water (2×10 mL), saturated NaHCO3 (10 mL)
  2. dry with materialwas dried (MgSO4)
  3. concentrationConcentration
  4. customgave 48 mg which
  5. stirringthe mixture was stirred for 2 hr
  6. customThe excess base was quenched by addition of 0.1 mL of acetic acid
  7. filtrationthe solution was filtered through a 0.2μ nylon
  8. filtrationfilter
  9. customthe filtrate was purified by RP-HPLC on a 4×30 cm Rainin C-18 column
  10. washThe peak eluting at 74.5% acetonitrile
  11. washmass 522.2393 (M+H), the peak eluting at 83% acetonitrile
  12. customwas recovered N-[[1-(phenylmethyl)cyclopentyl]carbonyl]-4-[(4-quinolinylcarbonyl)amino]-L-phenylalanine methyl ester (15 mg), HR—FAB—MS

출처 및 근거

ORD 기록
ord-8bf3c00632f64a78b26f7dbfe4f41c5f
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06806365B2

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