Potassium Phosphate, Tribasic → HCID 58266416、化合物

HRID 1505973ノート

反応式

HRID 1505973 の反応式
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]

参加物

6

反応物 2

HCID 62657Potassium Phosphate, TribasicHCID 58266539HCID 58266539、化合物

生成物 1

HCID 58266416HCID 58266416、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 14797Potassium Hydroxide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8ef6c30eb6c044199b7a4c460784f206
出典データセット
uspto-grants-2015_12
特許番号
US09216980B2

反応ノート

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