Dimethylformamide dimethyl acetal → HCID 54413822, compound

HRID 1419146Notes

Reaction equation

HRID 1419146 reaction equation
CN1C[CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH:16][C:17]4[C:22]([N+]([O-])=O)=[CH:21][CH:20]=[CH:19][N:18]=4)[CH:14]=3)[NH:9][CH:8]=2)C1.CO[CH:28](OC)[N:29]([CH3:31])[CH3:30].C(OCC)(=O)C.CO.[CH2:42]([N:44](CC)CC)C>>[CH3:30][N:29]1[CH2:31][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N:16]4[C:20]5[C:19](=[N:44][CH:42]=[CH:22][CH:21]=5)[NH:18][CH2:17]4)[CH:14]=3)[NH:9][CH:8]=2)[CH2:28]1

Participants

4

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 54920873-(1-Methylpyrrolidin-3-yl)-N-(3-nitropyridin-2-yl)-1H-indol-5-amineHCID 21980445Ethyl acetate methanol triethylamine

Product 1

HCID 54413822HCID 54413822, compoundYield 24%

Procedure

3-(N-Methylpyrrolidin-3-yl)-5-(3-nitropyrid-2-ylamino)-1H-indole was used. Reduction was by catalytic hydrogenation, the cyclization reaction used dimethylformamide dimethylacetal, and the cyclization reaction was heated for 24 hours. Chromatography using 9:1:1 [ethyl acetate/methanol/triethylamine] afforded the title compound (24%) as a white solid: mp, 110.0°-112.0° C.; 13C NMR (CDCl3) δ 147.7, 144.8, 144.3, 136.2, 135.7, 128.3, 127.3, 126.8, 122.4, 119.0, 118.7,115.6, 112.4, 62.3, 56.2, 42.2, 34.9, 32.1. HRMS calculated for C19H19N5 317.1643, found 317.1665. Anal. calcd for C19H19N5.0.5 C4H8O4 [ethyl acetate].0.5 H2O: C, 68.08; H, 6.53; N, 18.90. Found: C, 67.93; H, 6.51; N, 19.17.

Workup

  1. customthe cyclization reaction
  2. customthe cyclization reaction
  3. temperaturewas heated for 24 hours

Sources & evidence

ORD record
ord-29215c6730644b8d8c8791f637a08b7c
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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