Hydrochloric Acid → HCID 58465961、化合物

HRID 455684ノート

反応式

HRID 455684 の反応式
C[Al](C)C.C1(C)C=CC=CC=1.[NH2:12][C:13]1([CH2:29][O:30][CH:31]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[C:32]#[N:33])[C:26]2[CH:25]=[C:24]([Cl:27])[N:23]=[CH:22][C:21]=2[O:20][C:19]2[C:14]1=[CH:15][C:16]([Br:28])=[CH:17][CH:18]=2.Cl>ClCCCl.C(Cl)Cl>[Br:28][C:16]1[CH:15]=[C:14]2[C:13]3([N:12]=[C:32]([NH2:33])[CH:31]([CH:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)[O:30][CH2:29]3)[C:26]3[CH:25]=[C:24]([Cl:27])[N:23]=[CH:22][C:21]=3[O:20][C:19]2=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 16682925TrimethylaluminumHCID 86658386HCID 86658386、化合物

生成物 1

HCID 58465961HCID 58465961、化合物

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Trimethylaluminum, as a 2 M solution in toluene, (0.973 ml, 1.947 mmol) was added dropwise via syringe to a solution of 2-((5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)methoxy)-2-cyclohexylacetonitrile (0.563 g, 1.217 mmol) in DCE (12 ml) at RT. After stirring 14 hours, the reaction was cooled to 0° C. and 1 N aq. HCl (12 ml, 12 mmol) was added dropwise via syringe (slowly at first until vigorous reaction subsided) and the mixture was stirred at 0° C. for 10 minutes and then at RT before being diluted with DCM. The layers were separated and the aqueous layer was extracted with DCM. The combined organic extracts were washed with 1 N aq. NaOH, saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel chromatography by eluting with 1:20 MeOH in DCM, to provide 7-bromo-3-chloro-6′-cyclohexyl-2′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,3′-[1,4]oxazin]-5′-amine as a mixture of racemic diastereomers. [M+H]=462.0.

後処理

  1. customfirst until vigorous reaction
  2. stirringwas stirred at 0° C. for 10 minutes
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM
  5. washThe combined organic extracts were washed with 1 N aq. NaOH, saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo
  9. customto give the crude material
  10. customThe crude material was purified by silica gel chromatography
  11. washby eluting with 1:20 MeOH in DCM

出典と根拠

ORDレコード
ord-c7593c49ef8b4002986440e6cdf59be5
出典データセット
uspto-grants-2013_07
特許番号
US08497264B2

反応ノート

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