Ammonium Chloride → 2-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)thiazole-5-carboxamide

HRID 561200ノート

反応式

HRID 561200 の反応式
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17](O)=[O:18])=[CH:15][N:16]=2)[CH2:8][CH2:7]1.C1C=CC2N(O)N=[N:32]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:25][C:2]([F:1])([F:24])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[S:13][C:14]([C:17]([NH2:32])=[O:18])=[CH:15][N:16]=2)[CH2:10][CH2:11]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 666968024-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl-1,3-thiazole-5-carboxylic acid

生成物 1

HCID 468806672-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)thiazole-5-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carboxylic acid (14.5 g, 39 mmol), HOBt (5.3 g, 39 mmol)), HATU (23.7 g, 62 mmol) and NH4Cl (6.3 g, 117 mmol) in DMF (200 mL) at room temperature was added Hünig's base (34 mL, 195 mmol) over about 15 min. The mixture was stirred at room temperature overnight. After dilution with water, the mixture was extracted twice with EtOAc. The EtOAc extracts were combined, washed with 0.5 N NaOH (2×), diluted brine (1×), 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): δ7.79 (s, 1H), 7.67-7.61 (m, 2H), 7.38 (d, 1H), 7.12 (t, 1H), 5.02 (s, 1H), 3.76 (t, 2H), 3.71-3.67 (m, 2H), 2.16 (t, 2H), 2.00-1.94 (m, 2H).

後処理

  1. extractionAfter dilution with water, the mixture was extracted twice with EtOAc
  2. washwashed with 0.5 N NaOH (2×), diluted brine (1×)
  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-4be4b7674a2e4ecebaf94970fa96e13c
出典データセット
uspto-grants-2011_11
特許番号
US08063224B2

反応ノート

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