Trifluoroacetic acid → 4-[5-({[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]amino}carbonyl)-1H-indazol-3-yl]pyridinium trifluoroacetate

HRID 1467307ノート

反応式

HRID 1467307 の反応式
[C:1]([C:3]1[CH:52]=[CH:51][CH:50]=[CH:49][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:19]=[C:18]3[C:43]2[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=2)=[O:14])[CH2:7]1)#[N:2].[C:53]([OH:59])([C:55]([F:58])([F:57])[F:56])=[O:54]>>[F:56][C:55]([F:58])([F:57])[C:53]([O-:59])=[O:54].[C:1]([C:3]1[CH:52]=[CH:51][CH:50]=[CH:49][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:43]2[CH:44]=[CH:45][NH+:46]=[CH:47][CH:48]=2)=[O:14])[CH2:7]1)#[N:2]

参加物

3

反応物 2

HCID 6422Trifluoroacetic acidHCID 86681276N-[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]-3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxamide

生成物 1

HCID 866812774-[5-({[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]amino}carbonyl)-1H-indazol-3-yl]pyridinium trifluoroacetate

実験手順

To a microwave vial equipped with a stir bar was added N-[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]-3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxamide (41.7 mg, 0.061 mmol) and TFA (1000 μl, 12.98 mmol). The reaction was stirred at room temperature for 20 minutes. After 20 minutes the LCMS indicates formation of the desired product. Triethylsilane (19.62 μl, 0.123 mmol) was addes, and the crude reaction was concentrated in vacuo. The crude was dissolved in 1 ml DMSO, filtered, and purified by reverse phase chromatography. The material was concentrated, and was then dissolved in acetonitrile and water. The compound was dried on the lyophilizer over 2 days to provide fluffy white solid. LCMS calc'd for C26H25N6O [M+H]+=437; found 437 1H NMR (600 MHz, CD3OD) δ 8.9 (d, 2H), 8.9 (s, 1H), 8.7 (d, 2H), 8.0 (d, 1H), 7.9 (d, 1H), 7.8 (s, 2H), 7.8 (d, 1H), 7.7 (m, 1H), 4.6 (s, 2H), 4.4 (m, 1H), 3.7 (m, 1H), 3.6 (m, 1H), 3.2 (m, 2H), 2.2 (m, 2H), 2.0 (m, 1H), 1.8 (m, 1H).

後処理

  1. customTo a microwave vial equipped with a stir bar
  2. waitAfter 20 minutes the LCMS indicates

出典と根拠

ORDレコード
ord-759af97709a3425e8a0584b4cf8751d1
出典データセット
uspto-grants-2015_04
特許番号
US08999957B2

反応ノート

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