2-Aminobenzimidazole → HCID 58362664, compound

HRID 2361502Notes

Reaction equation

HRID 2361502 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=O.[NH2:16][C:17]1[NH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>C(O)(=O)C>[C:11]([C:10]1[CH:13]=[CH:14][C:7]([C:5]2[CH:4]=[CH:3][N:21]3[C:17](=[N:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=43)[N:16]=2)=[CH:8][CH:9]=1)#[N:12]

Participants

4

Reactant 2

HCID 136242-AminobenzimidazoleHCID 5714031HCID 5714031, compound

Product 1

HCID 58362664HCID 58362664, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (E)-4-(3-(dimethylamino)acryloyl)benzonitrile (2.0 g, 10.0 mmol) and 2-aminobenzimidazole (1.33 g, 10 mmol) in acetic acid (15 mL) was heated at 120° C. for 16 hours. The mixture was concentrated to a residue and treated with sodium bicarbonate solution to neutralize the residual acetic acid. The resulting suspension was added EtOAc, sonicated, and filtered. The solid collected was washed with water, ether, and dried under high vacuum to give 630 mg (23%) of T709 as yellow solid. A small amount was purified by HPLC (acetonitrile/H2O) for NMR and bioassay. 1H NMR (CD3OD): δ 9.83 (1H, d, J=8.4 Hz), 8.59 (2H, m), 8.46 (1H, d, J=8.4 Hz), 8.36 (1H, d, J=6.8 Hz), 8.01 (2H, m), 7.93 (1H, m), 7.87 (1H, m), 7.74 (1H, m); MS: 271 (M+H+).

Workup

  1. concentrationThe mixture was concentrated to a residue
  2. additiontreated with sodium bicarbonate solution
  3. additionThe resulting suspension was added EtOAc
  4. customsonicated
  5. filtrationfiltered
  6. customThe solid collected
  7. washwas washed with water, ether
  8. customdried under high vacuum
  9. customto give 630 mg (23%) of T709 as yellow solid
  10. customA small amount was purified by HPLC (acetonitrile/H2O) for NMR and bioassay

Sources & evidence

ORD record
ord-dd8c0184497d4585969c10ca3911e36c
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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