Potassium Phosphate, Tribasic → HCID 58266416, 화합물

HRID 1888512노트

반응식

HRID 1888512 반응식
C1(S([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[C:23]([C:26]4[CH:31]=[CH:30][C:29]([CH2:32][N:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[CH:28][CH:27]=4)[CH:24]=[N:25][C:11]2=3)(=O)=O)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[OH-].[K+].CO.O>[OH:19][C:18]1[C:13]2[C:12]3[CH:22]=[C:23]([C:26]4[CH:31]=[CH:30][C:29]([CH2:32][N:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[CH:28][CH:27]=4)[CH:24]=[N:25][C:11]=3[NH:10][C:14]=2[CH:15]=[N:16][C:17]=1[C:20]#[N:21]

참가 물질

6

반응물 2

HCID 62657Potassium Phosphate, TribasicHCID 58266539HCID 58266539, 화합물

생성물 1

HCID 58266416HCID 58266416, 화합물

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 14797Potassium Hydroxide용매

실험 절차

9-Benzenesulfonyl-5-hydroxy-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (50 mg, 0.01 mmol) was dissolved in 0.15N potassium hydroxide solution in methanol (7 mL). The reaction mixture was stirred for 2.5 h then treated with a solution of monobasic potassium phosphate (136 mg, 1.0 mmol) in water (2 mL). The resultant mixture was concentrated in vacuo and the resultant residue was diluted with water (5 mL). The pH of the aqueous phase was adjusted to 7 by the addition of 1N hydrochloric acid. The aqueous phase was extracted with ethyl acetate, DCM and THF. The combined organic phase was concentrated in vacuo and the residue purified by flash chromatography (silica, 500 mg column, Si-SPE, 10-20% methanol in DCM) to afford the title compound as its hydrochloride salt (25 mg, 63%). 1H NMR (DMSO-D6, 400 MHz): 12.91 (s, 1H), 11.86 (br. s, 1H), 10.41 (s, 1H), 9.13 (d, J=2.2 Hz, 1H), 9.00 (d, J=2.2 Hz, 1H), 8.60 (s, 1H), 7.93 (d, J=8.1 Hz, 2H), 7.76 (d, J=8.1 Hz, 2H), 4.33 (d, J=5.2 Hz, 2H), 3.39-3.29 (m, 2H), 2.92-2.83 (m, 2H), 1.85-1.63 (m, 5H), 1.45-1.31 (m, 1H). LCMS (Method A): RT=5.32 min, M+H+=384.

후처리

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. additionthe resultant residue was diluted with water (5 mL)
  3. additionThe pH of the aqueous phase was adjusted to 7 by the addition of 1N hydrochloric acid
  4. extractionThe aqueous phase was extracted with ethyl acetate, DCM and THF
  5. concentrationThe combined organic phase was concentrated in vacuo
  6. customthe residue purified by flash chromatography (silica, 500 mg column, Si-SPE, 10-20% methanol in DCM)

출처 및 근거

ORD 기록
ord-1581b99838cf4e518f5cb67582d40383
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501765B2

반응 노트

불러오는 중…