1,2-Dichloroethane → (+/-)-3-Bromo-2-methyl-N-[2-methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]benzamide

HRID 20841

反応式

HRID 20841 の反応式
C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[Br:15][C:16]1[C:17]([CH3:25])=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([OH:21])=O.[CH3:26][C:27]([N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1)([CH3:36])[CH:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[N-]=C=O>C(Cl)Cl.C1COCC1.CN1C(=O)CCC1>[Br:15][C:16]1[C:17]([CH3:25])=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH:35][CH:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:27]([CH3:36])([N:37]1[CH2:38][CH2:39][CH2:40][CH2:41]1)[CH3:26])=[O:21]

参加物

9

反応物 5

HCID 111,2-DichloroethaneHCID 105034IsocyanateHCID 181649HOAtHCID 27355903-Bromo-2-methylbenzoic AcidHCID 25158607[2-Methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]amine

生成物 1

HCID 59347855(+/-)-3-Bromo-2-methyl-N-[2-methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]benzamide収率 84%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To PS-EDC (0.068 g; 0.1 mmol; 1.42 mmol/g) was added a solution of HOAt (0.01 mmol in 0.8 ml (THF:DCM, 1:1)) followed by the addition of 3-bromo-2-methyl-benzoic acid (0.011 g; 0.05 mmol) in 1:3 NMP:THF (0.25 ml) and then [2-methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]amine D5 (0.011 g 0.05 mmol) in DCM (0.25 ml). The reaction was allowed to mix for 60 h. Following this PS-isocyanate (0.068 g, 0.1 mmol, 1.5 mmol/g) and PS—CO3 (0.068 g, 0.1 mmol, 1.5 mmol/g) were added and allowed to mix for another 24 h. The reaction mixture was filtered and passed through an SCX block (500 mg) (pre-wetted with DCM). The content of the Robbins block was washed with more solvent (DCM:THF, 1:1) and allowed to pass through the SCX which was then washed with DCM (2 ml×2) and methanol (2 ml×2). The SCX was then eluted with 0.5M ammonia in methanol and the product containing eluent evaporated to afford the title product (17.4 mg; 84%). Mass Spectrum (Electrospray LC/MS): Found 414 (MH+). C22H2779BrN2O requires 415; Ret. time 2.64 min*

後処理

  1. additionto mix for 60 h
  2. additionwere added
  3. additionto mix for another 24 h
  4. filtrationThe reaction mixture was filtered
  5. washThe content of the Robbins block was washed with more solvent (DCM:THF, 1:1)
  6. washwas then washed with DCM (2 ml×2) and methanol (2 ml×2)
  7. washThe SCX was then eluted with 0.5M ammonia in methanol
  8. additionthe product containing eluent
  9. customevaporated

出典と根拠

ORDレコード
ord-a06ba00a06924488961616c83a3158f1
出典データセット
uspto-grants-2010_06
特許番号
US07745642B2

関連ノート

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