Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → N-cyclobutyl-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxamide

HRID 1713133ノート

反応式

HRID 1713133 の反応式
Cl.[CH:2]1([NH:6][C:7]([C:9]2[CH:18]=[CH:17][C:16]3[CH2:15][N:14]([CH2:19][C:20]([OH:22])=O)[CH2:13][CH2:12][C:11]=3[N:10]=2)=[O:8])[CH2:5][CH2:4][CH2:3]1.[CH:23]1([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH2:26][CH2:25][CH2:24]1.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(Cl)Cl>[CH:2]1([NH:6][C:7]([C:9]2[CH:18]=[CH:17][C:16]3[CH2:15][N:14]([CH2:19][C:20]([N:30]4[CH2:31][CH2:32][N:27]([CH:23]5[CH2:26][CH2:25][CH2:24]5)[CH2:28][CH2:29]4)=[O:22])[CH2:13][CH2:12][C:11]=3[N:10]=2)=[O:8])[CH2:3][CH2:4][CH2:5]1

参加物

5

反応物 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 47386021-CyclobutylpiperazineHCID 66877729{2-[(cyclobutylamino)carbonyl]-7,8-dihydro-1,6-naphthyridin-6(5H)-yl}acetic acid hydrochloride

生成物 1

HCID 59463539N-cyclobutyl-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of {2-[(cyclobutylamino)carbonyl]-7,8-dihydro-1,6-naphthyridin-6(5H)-yl}acetic acid hydrochloride (37 mg, 0.11 mmol), 1-cyclobutylpiperazine (19 mg, 0.133 mmol), BOP (59 mg, 0.133 mmol) and TEA (0.075 ml, 0.532 mmol) in DCM (5 ml) is stirred at rt overnight. The solvent is removed in vacuo and the residue is partitioned between water (10 mL) and EtOAc (10 mL). The layers are separated and the aqueous layer is extracted with EtOAc (10 ml). The combined extracts are washed with brine (10 mL), dried and evaporated. The residue is purified by PTLC to give the title compound as a light yellow oil. MS (M+1): 412.4; 1H NMR (δ, CDCl3): 8.11 (d, 1H), 7.94 (d, 1H), 7.43 (d, 1H), 4.53-4.61 (m, 1H), 3.75 (s, 2H), 3.58-3.66 (m, 4H), 3.45 (t, 2H), 3.40 (s, 2H), 3.04 (t, 2H), 2.92 (t, 2H), 2.63-2.76 (m, 1H), 2.36-2.46 (m, 2H), 2.25-2.32 (m, 6H), 1.63-2.06 (m, 6H).

後処理

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between water (10 mL) and EtOAc (10 mL)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 ml)
  5. washThe combined extracts are washed with brine (10 mL)
  6. customdried
  7. customevaporated
  8. customThe residue is purified by PTLC

出典と根拠

ORDレコード
ord-2dc04d11e7f94256ac76cb3ec97dd594
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

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