Triethylamine → HCID 11646002、化合物

HRID 408524ノート

反応式

HRID 408524 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]([OH:14])=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:15]1([C:21]2[N:22]=[C:23]([NH2:26])[S:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(#N)C>[C:15]1([C:21]2[N:22]=[C:23]([NH:26][C:12]([C:9]3([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[CH2:10][CH2:11]3)=[O:14])[S:24][CH:25]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 403022-Amino-4-phenylthiazoleHCID 855751-(4-Methoxyphenyl)cyclopropane-1-carboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

生成物 1

HCID 11646002HCID 11646002、化合物収率 47.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1-(4-Methoxy-phenyl)-cyclopropanecarboxylic acid (2.18 g, 11.4 mmol) and 4-phenyl-thiazol-2-ylamine (2.00 g, 11.4 mmol) were dissolved in acetonitrile (50 mL) containing triethylamine (3.17 mL, 22.8 mmol). Benzotriazol-1-yloxy tris(dimethylamino)-phosphonium hexafluorophosphate (BOP, 4.95 g, 11.4 mmol) was added and the solution was allowed to stir for 64 hours. The reaction mixture was evaporated to dryness and purified by column chromatography on silica gel using a gradient of 5-20% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a white solid (1.9 g, 5.43 mmol, 47.5%). ESI-MS m/z calc. 350.1. found 351.1 (M+1)+. Retention time of 3.68 minutes. 1H NMR (400 MHz, CD3CN) δ 1.27 (q, J=3.6 Hz, 2H), 1.66 (q, J=3.6 Hz, 2H), 3.87 (s, 3H), 7.04 (m, 2H), 7.40 (m, 6H), 7.82 (m, 2H), 8.79 (s, 1H).

後処理

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by column chromatography on silica gel using a gradient of 5-20% ethyl acetate in hexanes
  3. customevaporated to dryness

出典と根拠

ORDレコード
ord-2d06ef28640045d79a67ac94dd9784fc
出典データセット
uspto-grants-2014_06
特許番号
US08759335B2

反応ノート

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