Diisopropylethylamine → HCID 67427797、化合物

HRID 1295127ノート

反応式

HRID 1295127 の反応式
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([OH:14])=O.[CH2:15]([O:17][C:18](=[O:34])[CH2:19][CH:20]([N:24]1[C:32]2[C:27](=[CH:28][C:29]([NH2:33])=[CH:30][CH:31]=2)[CH:26]=[CH:25]1)[CH2:21][CH2:22][CH3:23])[CH3:16].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)C)CC)(C)C>CN(C=O)C>[CH2:15]([O:17][C:18](=[O:34])[CH2:19][CH:20]([N:24]1[C:32]2[C:27](=[CH:28][C:29]([NH:33][C:12](=[O:14])[CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[CH2:6][CH2:7][CH2:8][NH:9][C:10]=4[N:1]=3)=[CH:30][CH:31]=2)[CH:26]=[CH:25]1)[CH2:21][CH2:22][CH3:23])[CH3:16]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22570252(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)acetic acidHCID 674273453-(5-Amino-indol-1-yl)-hexanoic acid ethyl ester

生成物 1

HCID 67427797HCID 67427797、化合物収率 68.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of (5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-acetic acid (0.2 g, 0.65 mmol), 3-(5-amino-indol-1-yl)-hexanoic acid ethyl ester (0.19 g, 0.71 mmol), BOP (0.35 g, 0.78 mmol), and diisopropylethylamine (0.45 mL, 2.6 mmol) in DMF (2.5 mL) was stirred for 16 h. Solvents were evaporated. The resulting residue was partitioned between H2O and EtOAc. The aqueous layer was separated and extracted once more with EtOAc. The extracts were combined, washed with H2O, brine, dried over Na2SO4, concentrated, and flash chromatographed on silica gel, eluting with EtOAc/DCM (15, 30, 50, and 80%) to give the title compound (0.20 g, 67% yield) as a brown oil. Mass spectrum (LCMS, ESI) calculated for C26H33N4O3 449.3 (M+H); found 449.3.

後処理

  1. customSolvents were evaporated
  2. customThe resulting residue was partitioned between H2O and EtOAc
  3. customThe aqueous layer was separated
  4. extractionextracted once more with EtOAc
  5. washwashed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customflash chromatographed on silica gel
  9. washeluting with EtOAc/DCM (15, 30, 50, and 80%)

出典と根拠

ORDレコード
ord-45ee0778ff7146cda1aa6589ea0b95c0
出典データセット
uspto-grants-2007_07
特許番号
US07241789B2

反応ノート

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