Benzoic Acid → HCID 59674098, compound

HRID 1391634Notes

Reaction equation

HRID 1391634 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:22][N:23]([C:35]1[CH:40]=[CH:39][N:38]=[C:37]([NH:41][C:42]2[CH:47]=[CH:46][C:45]([CH2:48][S:49]([CH3:52])(=[O:51])=[O:50])=[CH:44][CH:43]=2)[N:36]=1)[C:24]1[CH:34]=[CH:33][C:27]2[N:28]([CH3:32])[C:29]([NH2:31])=[N:30][C:26]=2[CH:25]=1.C(N(CC)CC)C>CN(C)C=O>[CH3:32][N:28]1[C:27]2[CH:33]=[CH:34][C:24]([N:23]([CH3:22])[C:35]3[CH:40]=[CH:39][N:38]=[C:37]([NH:41][C:42]4[CH:43]=[CH:44][C:45]([CH2:48][S:49]([CH3:52])(=[O:50])=[O:51])=[CH:46][CH:47]=4)[N:36]=3)=[CH:25][C:26]=2[N:30]=[C:29]1[NH:31][C:1](=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 59674094HCID 59674094, compound

Product 1

HCID 59674098HCID 59674098, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of benzoic acid (51 mg, 0.402 mmol) in N,N-dimethylformamide (2 ml) was added 1,1′-carbonyldiimidazole (65.2 mg, 0.400 mmol). The mixture was stirred for 30 minutes at room temperature and then a solution of N5,1-dimethyl-N5-[2-({4-[(methylsulfonyl)methyl]phenyl}amino)pyrimidin-4-yl]-1H-benzimidazole-2,5-diamine (88 mg, 0.201 mmol) and triethylamine (0.03 ml, 0.201 mmol) in N,N-dimethylformamide (2 ml) was added. The reaction mixture was stirred for 16 h, quenched with saturated sodium bicarbonate solution (30 ml) and the product then precipitated. The crude product was filtered, washed with water, diethyl ether and air dried to give the desired product without further purification. 1H NMR (400 MHz, d6-DMSO) δ 12.82 (s, 1H), 9.28 (s, 1H), 8.28 (d, J=7.3 Hz, 2H), 7.89 (d, J=6.1 Hz, 1H), 7.74 (d, J=8.2 Hz, 2H), 7.59 (d, J=8.4 Hz, 1H), 7.51-7.44 (m, 4H), 7.25-7.20 (m, 3H), 5.79 (d, J=5.9 Hz, 1H), 4.34 (s, 2H), 3.77 (s, 3H), 3.47 (s, 3H), 2.84 (s, 3H). MS (ESI) m/z=542 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred for 16 h
  2. customquenched with saturated sodium bicarbonate solution (30 ml)
  3. customthe product then precipitated
  4. filtrationThe crude product was filtered
  5. washwashed with water, diethyl ether and air
  6. customdried

Sources & evidence

ORD record
ord-13ec0bb5c04f41a4bda63eee8e6de90a
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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