Sodium Hydroxide → HCID 178479332, 화합물

HRID 81313

반응식

HRID 81313 반응식
Cl.[NH:2]1[CH:6]=CC(C(N)=N)=N1.[NH2:10][CH2:11][CH2:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.C([N:23](C(C)C)CC)(C)C.CO[C:31]([C:33]1[C:38]([NH2:39])=[N:37][C:36]([NH2:40])=[C:35]([Cl:41])[N:34]=1)=[O:32].[OH-].[Na+]>CN(C=O)C.CO.CCOCC>[ClH:41].[NH2:17][C:16]1[CH:18]=[CH:19][C:13]([CH2:12][CH2:11][NH:10][C:6]([N:37]2[C:36]([NH2:40])=[C:35]([Cl:41])[N:34]=[C:33]([C:31]([NH2:23])=[O:32])[CH:38]2[NH2:39])=[NH:2])=[CH:14][CH:15]=1

참가 물질

9

반응물 5

HCID 14798Sodium HydroxideHCID 728952-(4-Aminophenyl)ethylamineHCID 73827Methyl 3,5-diamino-6-chloropyrazine-2-carboxylateHCID 81531DiisopropylethylamineHCID 178479321HCID 178479321, 화합물

생성물 1

HCID 178479332HCID 178479332, 화합물수율 11%

시약·촉매·용매 3

HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1-H-pyrazolecarboxamidine hydrochloride (2.8 g, 19 mmol), 4-aminoethylaniline (1.3 mL, 9 mmol) and diisopropylethylamine (1.3 ml) were stirred in dry DMF (5 mL) under argon for 18 h. After this time, ether (30 ml) was added to produce a clear oil. The obtained oil (82) was washed with ether and dried under vacuum (40 mTorr) overnight. After drying 70 mg of oil was taken into dry methanol (3 mL) and 25% NaOH (0.14 mL) was added. The reaction volume was decreased to 1.0 mL and 3,5-diamino-6-chloropyrazine-2 carboxylic acid methyl ester (0.1 g, 0.5 mmol) was added. The mixture was stirred at room temperature overnight. Another portion of 82 (0.1 g) was dissolved in methanol (1 mL), treated with 25% NaOH (0.15 mL) and the resulting solution was added to the reaction mixture. The reaction mixture was stirred 3 h at reflux, then cooled to room temperature and the solvent was removed under reduced pressure. The residue was dissolved in a minimal volume of DMF and separated by preparative HPLC. The obtained fractions were analyzed by LC/MS. The fractions containing product with M+H=349 were collected and the solvent was removed under reduced pressure. The residue was dissolved in 10% HCl and evaporated to dryness to produce 83 (23.5 mg, 11%) as a yellow solid. 1H NMR (360 MHz, DMSO-d6) δ 2.91 (m, 2H), 3.59 (m, 2H), 7.31 (d, 2H), 7.42 (m, 4H), 9.02 (br s., 2H), 9.41 (br s., 1H), 10.56 (s, 1H). 13C NMR (90 MHz, DMSO-d6) 33.1, 42.0, 108.9, 119.6, 120.7, 129.9 (2C), 131.0 (2C), 153.1, 154.1, 155.8, 165.2. API MS m/z=349 [C14H17ClN8O+H]+.

후처리

  1. customto produce a clear oil
  2. washThe obtained oil (82) was washed with ether
  3. customdried under vacuum (40 mTorr) overnight
  4. dry with materialAfter drying 70 mg of oil
  5. additionwas added
  6. additionwas added
  7. additionthe resulting solution was added to the reaction mixture
  8. stirringThe reaction mixture was stirred 3 h
  9. temperatureat reflux
  10. temperaturecooled to room temperature
  11. customthe solvent was removed under reduced pressure
  12. dissolutionThe residue was dissolved in a minimal volume of DMF
  13. customseparated by preparative HPLC
  14. additionThe fractions containing product with M+H=349
  15. customwere collected
  16. customthe solvent was removed under reduced pressure
  17. dissolutionThe residue was dissolved in 10% HCl
  18. customevaporated to dryness

출처 및 근거

ORD 기록
ord-2b170473052f42358e0ed61cd3f9a033
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846688B2

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