4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 10078061、化合物

HRID 346799ノート

反応式

HRID 346799 の反応式
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6]([N:15]([CH3:17])[CH3:16])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[K].[F:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][CH:42]=[C:41]2[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52](O)=[O:53]>CO>[CH3:16][N:15]([CH3:17])[C:6]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4][CH:3]([CH2:2][NH:1][C:52](=[O:53])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][C:41]2[C:40]3[C:44](=[CH:45][CH:46]=[C:38]([F:37])[CH:39]=3)[NH:43][CH:42]=2)[CH2:8][CH2:7]1

参加物

6

反応物 4

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 5462222PotassiumHCID 21082140HCID 21082140、化合物HCID 21082146(4-Aminomethyl-1-phenylcyclohexyl)dimethylamine

生成物 1

HCID 10078061HCID 10078061、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of the diastereoisomers of (4-aminomethyl-1-phenylcyclohexyl)dimethylamine (347 mg, 1.49 mmol.) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (620 mg, 2.2 mmol.) was added to a solution of the potassium salt of 6-(5-fluoro-1H-indol-3-yl)hexanoic acid (430 mg, 1.49 mmol.) in abs. methanol (30 ml), and stirring was carried out for 3 d at RT. For working up, the mixture was concentrated, water (10 ml) and 2M HCl (15 ml) were added to the residue, and washing was carried out with ether (25 ml). The diethyl ether phase was separated off. The aqueous phase and oily drops contained therein were adjusted to pH 11 with 5M NaOH and extracted with EE (4×15 ml). The combined EE extracts were washed with 1M NaOH (2×2 ml), dried, filtered and concentrated. The residue was a diastereoisomeric mixture of the bases of the target product, which was separated by flash chromatography on silica gel (75 g) and purified (eluant: 1500 ml of methanol/EE 1:1). 192 mg of the non-polar diastereoisomer of 6-(5-fluoro-1H-indol-3-yl)hexanoic acid (4-dimethylamino-4-phenylcyclohexylmethyl)amide were obtained (m.p. 52–54° C.).

後処理

  1. concentrationthe mixture was concentrated
  2. additionwater (10 ml) and 2M HCl (15 ml) were added to the residue
  3. washwashing
  4. customThe diethyl ether phase was separated off
  5. extractionextracted with EE (4×15 ml)
  6. washThe combined EE extracts were washed with 1M NaOH (2×2 ml)
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additiona diastereoisomeric mixture of the bases of the target product, which
  11. customwas separated by flash chromatography on silica gel (75 g)
  12. custompurified (eluant: 1500 ml of methanol/EE 1:1)

出典と根拠

ORDレコード
ord-96dd4a254d37413983e154d6aa3b9c1d
出典データセット
uspto-grants-2007_02
特許番号
US07173045B2

反応ノート

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