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Guanidine → HCID 178479500、化合物

HRID 1766157
ノート
印刷プレビュー

反応式

HRID 1766157 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([C:16]([OH:18])=O)=[CH:8]1.[ClH:19].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:41][C:42]([NH2:44])=[NH:43]>O1CCCC1>[ClH:19].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([C:16]([NH:43][C:42]([NH2:44])=[NH:41])=[O:18])=[CH:8]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 3520GuanidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 211100571-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

生成物 1

HCID 178479500HCID 178479500、化合物

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
20 °C

実験手順

1-(Pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, 0.46 g (2.4 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.027 g (0,2 mmol) of 1-hydroxybenzotriazole were added to 0.59 g (10 mmol) of guanidine in 15 cm3 of tetrahydrofuran under an argon atmosphere. After stirring at a temperature in the region of 20° C. for 16 days, the reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa) and the residue was triturated in 20 cm3 of methanol and then filtered. The filtrate was concentrated to dryness under reduced pressure (2.7 kPa) and the residue was purified by flash chromatography on silica gel, elution being carried out with a 100% of dichloromethane to dichloromethane/methanol/triethylamine (50/48/2 by volume) gradient over 90 min. After concentrating the fractions comprising the expected product to dryness under reduced pressure (2.7 kPa), the solid obtained was triturated in 20 cm3 of ethanol and filtered off, affording 0.028 g of N-[1-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]guanidine hydrochloride in the form of a beige powder melting at 205–207° C. 1H N.M.R. spectrum (300 MHz, (CD3)2SO, 8 in ppm): from 7.30 to 7.45 (m, 2H), 8.08 (ddd, J=9, 8 and 2 Hz, 1H), 8.43 (dd, J=5 and 2 Hz, 1H), 8.59 (dd, J=5 and 2 Hz, 1H), 8.84 (dd, J=8 and 2 Hz, 1H), 8.89 (s, 1H), 8.95 (d, J=9 Hz, 1H).

後処理

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa)
  2. customthe residue was triturated in 20 cm3 of methanol
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure (2.7 kPa)
  5. customthe residue was purified by flash chromatography on silica gel, elution
  6. waitbeing carried out with a 100% of dichloromethane to dichloromethane/methanol/triethylamine (50/48/2 by volume) gradient over 90 min
  7. concentrationAfter concentrating the fractions
  8. customthe solid obtained
  9. customwas triturated in 20 cm3 of ethanol
  10. filtrationfiltered off

出典と根拠

ORDレコード
ord-b1669b99477c4603bf30e2d1143a872c
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07230007B2

反応ノート

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