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Hydrochloric Acid → N-(4-methylthiazol-2-yl)-3-(phenylthio)-5-((tetrahydropyran-4-ylidene)methyl)pyridin-2-amine hydrochloride

HRID 911815
ノート
印刷プレビュー

反応式

HRID 911815 の反応式
[ClH:1].[CH3:2][C:3]1[N:4]=[C:5]([NH:8][C:9]2[N:14]=[CH:13][C:12]([CH:15]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)O)=[CH:11][C:10]=2[S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[S:6][CH:7]=1.O.CC1C=CC(S(O)(=O)=O)=CC=1.Cl>C1(C)C=CC=CC=1>[ClH:1].[CH3:2][C:3]1[N:4]=[C:5]([NH:8][C:9]2[C:10]([S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:11][C:12]([CH:15]=[C:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][N:14]=2)[S:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 86631490(6-(4-methylthiazol-2-ylamino)-5-(phenylthio)Pyridin-3-yl)(tetrahydro-2H-pyran-4-yl)methanol hydrochloride

生成物 1

HCID 86631492N-(4-methylthiazol-2-yl)-3-(phenylthio)-5-((tetrahydropyran-4-ylidene)methyl)pyridin-2-amine hydrochloride収率 35%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

実験手順

A 10 mL round-bottomed flask was charged with (6-(4-methylthiazol-2-ylamino)-5-(phenylthio)pyridin-3-yl)(tetrahydro-2H-pyran-4-yl)methanol hydrochloride (125 mg, 0.278 mmol), 4-methylbenzenesulfonic acid hydrate (5.28 mg, 0.0278 mmol), Toluene (5 mL) and heated to reflux in dean stark trap for 24 7 hours. The reaction was cooled to ambient temperature and partitioned between saturated aqueous sodium bicarbonate and CH2Cl2. The organic layer was dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel (25% EtOAc in hexanes) to afford the title compound (42 mg, 35.0% yield) as after HCl salt formation. 1H NMR (CDCl3) δ 12.24 (bs, 1H), 8.18 (m, 1H), 7.71 (m, 1H), 7.54 (m, 2H), 7.30 (m, 3H), 6.40 (s, 1H), 6.20 (s, 1H), 3.78 (t, 2H), 3.65 (t, 2H), 2.45 (s, 3H), 2.42 (m, 4H). Mass spectrum (apci) m/z=396.2 (M+H—HCl).

後処理

  1. temperatureheated
  2. temperatureto reflux in dean stark trap for 24 7 hours
  3. custompartitioned between saturated aqueous sodium bicarbonate and CH2Cl2
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (25% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-125983461308458f833608906227c447
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08022223B2

反応ノート

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