Ammonium Chloride → 2-{3-[2-(Trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxamide

HRID 2355060ノート

反応式

HRID 2355060 の反応式
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:16]([OH:18])=O)=[CH:14][N:15]=2)[CH2:7]1.C1C=CC2N(O)N=[N:31]C=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-].CCN(C(C)C)C(C)C>CN(C=O)C>[F:23][C:2]([F:24])([F:1])[C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:16]([NH2:31])=[O:18])=[CH:14][N:15]=2)[CH2:7]1

参加物

7

反応物 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 684517792-{3-[2-(Trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylic acid

生成物 1

HCID 576528252-{3-[2-(Trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboxylic acid (860 mg, 2.4 mmol), HOBt (324 mg, 2.4 mmol), HATU (1.5 g, 3.8 mmol) and NH4Cl (385 mg, 7.2 mmol) in DMF at rt was added DIPEA (2.1 mL, 12 mmol). The mixture was stirred at rt overnight. After dilution with water, the mixture was extracted twice with EtOAc. The EtOAc extracts were combined, washed twice with 0.5 N NaOH, diluted brine, dried (Na2SO4) and concentrated. The residue was triturated with Et2O:hexanes (1:1) to give the title compound as a pale yellow solid. 1H NMR (500 MHz, acetone-d6): δ 7.79 (s, 1 H), 7.68-7.64 (m, 2 H), 7.39 (d, 1 H), 7.15 (t, 1 H), 5.48 (s, 1 H), 3.91 (m, 1 H), 3.78-3.62 (m, 4 H), 2.57-2.49 (m, 1 H), 2.44-2.40 (m, 1 H). MS (+ESI) m/z 358 (MH+).

後処理

  1. extractionAfter dilution with water, the mixture was extracted twice with EtOAc
  2. washwashed twice with 0.5 N NaOH, diluted brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was triturated with Et2O:hexanes (1:1)

出典と根拠

ORDレコード
ord-62f70e8fa56c4ad78097c13c1e24fff9
出典データセット
uspto-grants-2010_07
特許番号
US07754745B2

反応ノート

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