Diisopropylethylamine → 1,1-Dimethylethyl {1-[({6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}amino)carbonyl]cyclobutyl}carbamate

HRID 527555ノート

反応式

HRID 527555 の反応式
[CH3:1][C:2]([O:5][C:6]([NH:8][C:9]1([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:49][C:50]1([CH3:67])[C:54]2[C:55]([O:59][C:60]3[N:65]=[CH:64][C:63]([NH2:66])=[CH:62][CH:61]=3)=[CH:56][CH:57]=[CH:58][C:53]=2[O:52][CH2:51]1>CN(C=O)C>[CH3:49][C:50]1([CH3:67])[C:54]2[C:55]([O:59][C:60]3[N:65]=[CH:64][C:63]([NH:66][C:13]([C:9]4([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:10][CH2:11][CH2:12]4)=[O:15])=[CH:62][CH:61]=3)=[CH:56][CH:57]=[CH:58][C:53]=2[O:52][CH2:51]1

参加物

6

反応物 4

HCID 81531Diisopropylethylamine2 回HCID 1512646Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)-3 回HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2 回HCID 679580606-[(3,3-Dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinamine

生成物 1

HCID 866984251,1-Dimethylethyl {1-[({6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}amino)carbonyl]cyclobutyl}carbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclobutanecarboxylic acid (Intermediate 68, 20.16 mg) in dry N,Ndimethylformamide (3 ml), DIPEA (20.44 μl, 0.117 mmol) and then HATU (35.6 mg, 0.094 mmol) were added and the reaction mixture was stirred for 15 minutes at room temperature under argon. Then 6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinamine Intermediate 59, 20 mg) was added and the reaction mixture was stirred at 60° C. under argon during 12 hours. The reaction mixture was cooled down and a prestirred (15 min) solution of HATU (1 equiv), 1-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclobutanecarboxylic acid (1 equiv) and DIPEA (1 equiv) in 1 mL of dry DMF was added. The reaction mixture was heated under argon an additional 12 hours at 60° C. The reaction mixture was evaporated. The residue obtained was purified on silica gel (Companion instrument) with cyclohexane/ethylacetate as eluents from 100/0 to 70/30. This afforded the title compound (14 mg)

後処理

  1. stirringthe reaction mixture was stirred at 60° C. under argon during 12 hours
  2. temperatureThe reaction mixture was cooled down
  3. additionwas added
  4. temperatureThe reaction mixture was heated under argon an additional 12 hours at 60° C
  5. customThe reaction mixture was evaporated
  6. customThe residue obtained
  7. customwas purified on silica gel (Companion instrument) with cyclohexane/ethylacetate as eluents from 100/0 to 70/30

出典と根拠

ORDレコード
ord-75e1551452e649018e5b16f1c8d8eb5e
出典データセット
uspto-grants-2016_05
特許番号
US09346790B2

反応ノート

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