Dimethylformamide → HCID 131720606、化合物

HRID 1599066ノート

反応式

HRID 1599066 の反応式
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([N:13](C(C)C)C2C=CC(OC)=CC=2)=[O:12])[C:6]2[CH:25]=[CH:26][CH:27]=[CH:28][C:5]=2[N:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:3]1=[O:35].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2N=N1.[CH:63]1C=CC2N(O)N=N[C:67]=2[CH:68]=1.[NH:73]1[C:81]2[C:76](=[CH:77][CH:78]=[CH:79][CH:80]=2)[CH:75]=[C:74]1[C:82]([OH:84])=O.CN([CH:88]=[O:89])C>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH:68]([C:10]([C:50]1[CH:51]=[CH:46][C:47]([O:89][CH3:88])=[CH:48][CH:49]=1)([C:11](=[O:12])[NH2:13])[N:7]1[C:8](=[O:9])[CH:2]([NH:1][C:82]([C:74]2[NH:73][C:81]3[C:76]([CH:75]=2)=[CH:77][CH:78]=[CH:79][CH:80]=3)=[O:84])[C:3](=[O:35])[N:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:5]2[CH:28]=[CH:27][CH:26]=[CH:25][C:6]1=2)([CH3:67])[CH3:63]

参加物

8

反応物 5

HCID 6228DimethylformamideHCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18929586HCID 18929586、化合物

生成物 1

HCID 131720606HCID 131720606、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-(3-Amino-2,4-dioxo-5-pyrdin-2-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (276 mg), BOP (244 mg), HOBT (78 mg), DMAP (69 mg) and indole-2-carboxylic acid (98 mg) in DMF (1 ml) was stirred at rt for 18 h. The reaction mixture was diluted with ethyl acetate (15 ml), washed with 1N aqueous sodium hydroxide solution (2×15 ml), water (20 ml), brine (20 ml), dried (K2CO3) and concentrated in vacuo to afford the cude product. Purification by RP-HPLC utilizing a linear gradient (20% A, 80% B to 90% B, 10% C, 30 min) gave the title product (26.6 mg) as a white lyophile;Tr=21.3 min. 1H NMR (300 MHz, CDCl3); 0.98 (2×d, J=7 Hz, 6H), 3.68 (s, 3H), 4.17 (d J=16.6 Hz, 1H), 4.37 (d, J=16.8 Hz, 1H), 4.87 (sept, J=6.8 Hz, 1H), 5.40 (d, J =6.8 Hz, 1H), 6.40 (d, J=5.3 Hz, 1H), 6.75-6.84 (m, 5H), 6.92-6.99 (m, 2H), 7.07 (t, J=7.3 Hz, 1H), 7.09-7.2 (m, 4H), 7.24 (t, J=9.2 Hz, 1H), 7.40 (t, J=9.1 Hz, 2H), 7.52 (d J=7.9 Hz, 1H), 7.72 (m, 2H), 8.38 (d, J=4.4 Hz, 1H), 9.19 (s, 1H). m/z [MH]+ =617.

後処理

  1. washwashed with 1N aqueous sodium hydroxide solution (2×15 ml), water (20 ml), brine (20 ml)
  2. dry with materialdried (K2CO3)
  3. concentrationconcentrated in vacuo
  4. customto afford the cude product
  5. customPurification by RP-HPLC
  6. customa linear gradient (20% A, 80% B to 90% B, 10% C, 30 min)

出典と根拠

ORDレコード
ord-a7cf7e02f8d04b98abc053292cf44d54
出典データセット
uspto-grants-1998_04
特許番号
US05739129

反応ノート

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