Dimethylformamide → HCID 19101718, compound

HRID 1974643Notes

Reaction equation

HRID 1974643 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]2[N:15]([CH:30]3[CH2:32][CH2:31]3)[C:16]([CH2:18][C:19]([NH:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:20])=[N:17][C:13]=2[C:12]([F:33])=[C:11]([N:34]2[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]2)[C:10]=1[F:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)[CH:44]=[O:45]>>[CH2:1]([NH:8][C:9]1[C:14]2[N:15]([CH:30]3[CH2:32][CH2:31]3)[C:16]3=[CH:18][C:19](=[O:20])[N:21]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:44](=[O:45])[N:17]3[C:13]=2[C:12]([F:33])=[C:11]([N:34]2[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]2)[C:10]=1[F:41])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 19101709HCID 19101709, compound

Product 1

HCID 19101718HCID 19101718, compoundYield 21%

Procedure

2-[7-Benzylamino-1-cyclopropyl-4,6-difluoro-5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2yl]-N-benzyloxy-acetamide (2.6 g, 4.64 mmol) is reacted with N,N'-carbonyldiimidazole (1.5 g, 9.28 mmol) in dimethylformamide (50 ml) at room temperature for 1 day. At the end of the reaction, the volatiles are evaporated under reduced pressure and the residue chromatographed on silica gel (eluent: 5% methanol-dichloromethane). The relevant fractions are concentrated in vacuo until crystals form. Filtration affords 0.57 g of 6-benzylamino-2-benzyloxy-5-cyclopropyl-7,9-difluoro-8-(4-methyl-piperazin-1-yl)-1,2,3,5-tetrahydro-pyrimido[1,6-a]benzimidazole-1,3-dione as colorless crystals (21%): mp: 214° C.; NMR (DMSO-d6): 0.97 (m,2H),1.18(m,2H),2.23(s,3H),2.42(m,4H),3.13 (m,5H),4.35(d,J=6.5 Hz,2H),5.05(s,2H),5.36(s,1H),7.22-7.61 (m,11H).

Workup

  1. customAt the end of the reaction
  2. customthe volatiles are evaporated under reduced pressure
  3. customthe residue chromatographed on silica gel (eluent: 5% methanol-dichloromethane)
  4. concentrationThe relevant fractions are concentrated in vacuo until crystals
  5. customform
  6. filtrationFiltration

Sources & evidence

ORD record
ord-87b37ea42a9f4f55aab9d2a9509269eb
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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