Dimethylformamide → 2-[(R)-1-(3-Toluoyloxy-2-oxo-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-quinazolin-4-one

HRID 1350636ノート

反応式

HRID 1350636 の反応式
[NH2:1][C@@H:2]([C:6]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](=[O:23])[C:13]2[C:8](=[CH:9][C:10]([Cl:24])=[CH:11][CH:12]=2)[N:7]=1)[CH:3]([CH3:5])[CH3:4].CCN([CH:31]([CH3:33])[CH3:32])C(C)C.[C:34]1(C)[C:35]([C:40]([O:42]CC(=O)CBr)=[O:41])=[CH:36]C=C[CH:39]=1.[C:49](Cl)(=[O:56])[C:50]1C=CC=CC=1.[CH3:58]N(C=O)C>>[C:31]1([CH3:32])[CH:33]=[CH:39][CH:34]=[C:35]([C:40]([O:42][N:1]([CH2:58][C:49](=[O:56])[CH3:50])[C@@H:2]([C:6]2[N:15]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:14](=[O:23])[C:13]3[C:8](=[CH:9][C:10]([Cl:24])=[CH:11][CH:12]=3)[N:7]=2)[CH:3]([CH3:5])[CH3:4])=[O:41])[CH:36]=1

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 21015281(R)-2-(1-amino-2-methylpropyl)-3-benzyl-7-chloroquinazolin-4(3H)-oneHCID 865918921-Toluoyloxy-3-bromopropan-2-one

生成物 1

HCID 210969932-[(R)-1-(3-Toluoyloxy-2-oxo-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-quinazolin-4-one

実験手順

To 2-((R)-1-amino-2-methyl-propyl)-3-benzyl-7-chloro-3H-quinazolin-4-one (1.0 g, 2.9 mMol) in DMF (10 mL) was added DIEA (0.6 mL, 3.4 mMol) and 1-toluoyloxy-3-bromopropan-2-one (1.0 g, 3.7 mMol) (Prepared using the procedure of F. C. Hartman, Biochemistry, 9, 1776 (1970) except substituting toluoyl chloride for benzoyl chloride.) The reaction was stirred at RT for 18 h, concentrated under vacuum, taken up in EtOAc, washed with 1 N Na2CO3, dried (Na2SO4) and evaporated to dryness. The product was converted to its hydrochloride salt by treating with 4 N HCl in dioxane (20 mL) and concentration under vacuum. Trituration with (1:1) Et2O/pet. ether, filtration and drying under vacuum left the title compound (1.87 g, 100%, 88% pure) as a beige solid: MS (ES) m/e 532.2 (M+H)+.

後処理

  1. customPrepared
  2. concentrationconcentrated under vacuum
  3. washwashed with 1 N Na2CO3
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. additionby treating with 4 N HCl in dioxane (20 mL) and concentration under vacuum
  7. filtrationTrituration with (1:1) Et2O/pet. ether, filtration
  8. customdrying under vacuum
  9. waitleft the title compound (1.87 g, 100%, 88% pure) as a beige solid

出典と根拠

ORDレコード
ord-37b1174dc9f04dc3b02954e2b345af00
出典データセット
uspto-grants-2007_05
特許番号
US07214800B2

反応ノート

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