Diisopropylethylamine → 5-Pyridin-3-yl-thiophene-2-carboxylic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide

HRID 2367739ノート

反応式

HRID 2367739 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=2)[CH:2]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.Cl.[NH2:48][CH2:49][C:50]1[CH:51]=[C:52]([CH:67]=[CH:68][CH:69]=1)[C:53]([NH:55][C:56]1[CH:65]=[C:64]2[C:59]([CH2:60][CH2:61][N:62]([CH3:66])[CH2:63]2)=[CH:58][CH:57]=1)=[O:54]>CN(C=O)C>[CH3:66][N:62]1[CH2:61][CH2:60][C:59]2[C:64](=[CH:65][C:56]([NH:55][C:53]([C:52]3[CH:51]=[C:50]([CH:69]=[CH:68][CH:67]=3)[CH2:49][NH:48][C:12]([C:10]3[S:11][C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[CH:8][CH:9]=3)=[O:14])=[O:54])=[CH:57][CH:58]=2)[CH2:63]1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 47391005-pyridin-3-ylthiophene-2-carboxylic AcidHCID 666490723-(2-Methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)benzylamine dihydrochloride

生成物 1

HCID 566017395-Pyridin-3-yl-thiophene-2-carboxylic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide収率 87%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-pyridin-3-yl-thiophene-2-carboxylic acid (31 mg, 0.15 mmol) in DMF (1 mL) add Hunig's Base (0.10 mL, 0.54 mmol) and TBTU (52 mg, 0.16 mmol) and stir at rt for 20 min. To this add 3-aminomethyl-N-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamide dihydrochloride (50 mg, 0.1 mmol) and stir the solution for 18 h at rt. Concentrate the solution and purify the residue by prep-HPLC (10% to 90%, CH3CN/H2O) to provide the desired product 5-pyridin-3-yl-thiophene-2-carboxylic acid 3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide (62 mg, 0.087 mmol). MS, electrospray 483.8 (M+H), rt 0.88 min.

後処理

  1. concentrationConcentrate the solution
  2. custompurify the residue by prep-HPLC (10% to 90%, CH3CN/H2O)

出典と根拠

ORDレコード
ord-de159192e99b4818929f2dd6146aee08
出典データセット
uspto-grants-2014_04
特許番号
US08697911B2

反応ノート

読み込み中…