Dimethylformamide → HCID 131720606, 화합물

HRID 1599066노트

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HRID 1599066 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 131720606HCID 131720606, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a7cf7e02f8d04b98abc053292cf44d54
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05739129

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