1-Hydroxybenzotriazole → HCID 178487804、化合物

HRID 633807ノート

反応式

HRID 633807 の反応式
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:12]([OH:14])=O)[CH:10]=[CH:11][C:5]=2[S:4][CH2:3]1.[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]2[C:25]([N:26]=1)=[C:24]1[CH2:27][CH:28]([CH2:30][C@H:31]3[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33][CH2:32]3)[O:29][C:23]1=[CH:22][N:21]=2.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]2[C:25]([N:26]=1)=[C:24]1[CH2:27][CH:28]([CH2:30][C@H:31]3[CH2:36][CH2:35][C@H:34]([NH:37][C:12]([C:9]4[CH:10]=[CH:11][C:5]5[S:4][CH2:3][C:2](=[O:1])[NH:7][C:6]=5[CH:8]=4)=[O:14])[CH2:33][CH2:32]3)[O:29][C:23]1=[CH:22][N:21]=2

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7609933-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178487802HCID 178487802、化合物

生成物 1

HCID 178487804HCID 178487804、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid (31 mg, 0.14 mmol, 1.0 eq) is added at room temperature to a stirred solution of trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexylamine (47 mg, 0.14 mmol, 1.0 eq) in N,N-dimethylformamide (4 mL), followed by 1-hydroxybenzotriazole (24 mg, 0.16 mmol, 1.1 eq), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (32 mg, 0.16 mmol, 1.15 eq) and N,N-diisopropylethylamine (56 μL, 0.32 mmol, 2.25 eq). After 15 hours stirring at room temperature, solvent is evaporated and the residue is extracted with dichloromethane (3×10 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by preparative HPLC to afford 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid [trans-4-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-amide as a white lyophilized powder (16 mg, 21% yield).

後処理

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with dichloromethane (3×10 mL) and water (10 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product that
  7. customis purified by preparative HPLC

出典と根拠

ORDレコード
ord-9c7b61a897544325ac4f7c0220166143
出典データセット
uspto-grants-2016_04
特許番号
US09321788B2

反応ノート

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