Diisopropylethylamine → HCID 67268025、化合物

HRID 602518ノート

反応式

HRID 602518 の反応式
[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([CH3:26])[CH:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[N:61]1([CH2:67][C:68](O)=[O:69])[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]1>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:68](=[O:69])[CH2:67][N:61]2[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]2)=[C:21]([CH3:26])[CH:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:16])[F:18])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 201097Piperidin-1-yl-acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67266881HCID 67266881、化合物

生成物 1

HCID 67268025HCID 67268025、化合物収率 53%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (4-amino-3-methylphenyl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (15.2 mg, 40 mol) in DMF (100 μL) was added a solution of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 27.4 mg, 72 mol) in DMF (100 μL), followed by i-Pr2NEt (25 μL, 144 mol) and piperidin-1-yl-acetic acid (8.6 mg, 60 mol). The resulting mixture was shaken at room temperature for 3 hours after which it was diluted with ethyl acetate (10 mL), washed with saturated aqueous ammonium chloride (2×10 mL), dried over sodium sulfate, and evaporated. The residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures) to yield [3-methyl-4-(2-piperidin-1-yl-acetylamino)-phenyl]-(4-trifluoromethylbenzyl)-carbamic acid tert-butyl ester as a white solid (10.7 mg, 53%). This was dissolved in dichloromethane (200 μL) and trifluoroacetic acid (200 μL), and the solution was kept at room temperature for 30 minutes, after which volatiles were evaporated and the residue was dried in vacuo at 0.1 mmHg and +40° C. for 1 hour. The resulting trifluoroacetic acid addition salt of the title compound was obtained as a yellow semisolid in quantitative yield.

後処理

  1. washwashed with saturated aqueous ammonium chloride (2×10 mL)
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures)

出典と根拠

ORDレコード
ord-e8a4c14ebd344fbfad9a8ceebf8d5dce
出典データセット
uspto-grants-2011_03
特許番号
US07906537B2

反応ノート

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