Triethylamine → 2-(3,5-Bis-trifluoromethyl-phenyl)-n-[(3s,4r)-1-(4-ethynyl-cyclohexanecarbonyl)-4-phenyl-pyrrolidin-3-yl]-n-methyl-isobutyramide

HRID 1365933ノート

反応式

HRID 1365933 の反応式
[C:1]([CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=O)[CH2:5][CH2:4]1)#[CH:2].CCN(CC)CC.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[F:46][C:47]([F:77])([F:76])[C:48]1[CH:49]=[C:50]([C:58]([CH3:75])([CH3:74])[C:59]([N:61]([CH3:73])[C@H:62]2[C@H:66]([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[CH2:65][NH:64][CH2:63]2)=[O:60])[CH:51]=[C:52]([C:54]([F:57])([F:56])[F:55])[CH:53]=1>C1COCC1>[F:76][C:47]([F:46])([F:77])[C:48]1[CH:49]=[C:50]([C:58]([CH3:74])([CH3:75])[C:59]([N:61]([C@H:62]2[C@H:66]([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[CH2:65][N:64]([C:9]([CH:6]3[CH2:5][CH2:4][CH:3]([C:1]#[CH:2])[CH2:8][CH2:7]3)=[O:11])[CH2:63]2)[CH3:73])=[O:60])[CH:51]=[C:52]([C:54]([F:55])([F:56])[F:57])[CH:53]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 19373388trans-4-Ethynylcyclohexanecarboxylic acidHCID 59840126Rac-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-n-((3s,4r)-4-phenyl-pyrrolidin-3-yl)-isobutyramide

生成物 1

HCID 598401252-(3,5-Bis-trifluoromethyl-phenyl)-n-[(3s,4r)-1-(4-ethynyl-cyclohexanecarbonyl)-4-phenyl-pyrrolidin-3-yl]-n-methyl-isobutyramide収率 54%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 4-ethynyl-cyclohexanecarboxylic acid (commercially available) (6.5 mg, 0.043 mmol) in THF (2 ml) at RT were added Et3N (12 μl, 0.086 mmol), BOP (25 mg, 0.057 mmol) and rac-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-((3S,4R)-4-phenyl-pyrrolidin-3-yl)-isobutyramide (Intermediate VII-1) (20 mg, 0.043 mmol). Stirring was continued at 40° C. for 48 hours. Concentration and purification by preparative HPLC afforded 13.7 mg (54%) of the title compound.

後処理

  1. concentrationConcentration and purification by preparative HPLC

出典と根拠

ORDレコード
ord-7b92719049ae4935a58066e6e89a2453
出典データセット
uspto-grants-2011_02
特許番号
US07893062B2

反応ノート

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