Aniline → HCID 59674239, compound

HRID 1391633Notes

Reaction equation

HRID 1391633 reaction equation
[CH3:1][N:2]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=2)[N:15]=1)[C:3]1[CH:13]=[CH:12][C:6]2[N:7]([CH3:11])[C:8]([NH2:10])=[N:9][C:5]=2[CH:4]=1.[C:32]([N:39]1[CH:43]=[CH:42]N=C1)(N1C=CN=C1)=[O:33].N[C:45]1[CH:50]=CC=[CH:47][CH:46]=1>CN(C)C(=O)C>[CH3:11][N:7]1[C:6]2[CH:12]=[CH:13][C:3]([N:2]([CH3:1])[C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=4)[N:15]=3)=[CH:4][C:5]=2[N:9]=[C:8]1[NH:10][C:32]([NH:39][C:43]1[CH:42]=[CH:47][CH:46]=[CH:45][CH:50]=1)=[O:33]

Participants

5

Reactant 3

HCID 6115AnilineHCID 682631,1'-CarbonyldiimidazoleHCID 59674094HCID 59674094, compound

Product 1

HCID 59674239HCID 59674239, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N5,1-dimethyl-N5-[2-({4-[(methylsulfonyl)methyl]phenyl}amino)pyrimidin-4-yl]-1H-benzimidazole-2,5-diamine (150 mg, 0.343 mmol) in N,N-dimethylacetamide (3 ml) was added 1,1′-carbonyldiimidazole (167 mg, 1.03 mmol). The mixture was stirred for 24 h and then aniline (192 mg, 2.06 mmol) was added. The mixture was stirred for 2 h. The reaction was quenched with saturated sodium bicarbonate solution (30 ml) and the product precipitated. The crude product was filtered, washed with water, diethyl ether and air dried to give the desired product without further purification. 1H NMR (300 MHz, d6-DMSO) δ 12.14 (s, 1H), 9.26 (s, 1H), 9.12 (s, 1H), 7.86 (d, J=5.8 Hz, 1H), 7.76-7.68 (m, 4H), 7.42 (d, J=8.2 Hz, 1H), 7.30-7.20 (m, 5H), 7.12 (d, J=8.2 Hz, 1H), 6.89 (t, J=7.1 Hz, 1H), 5.75 (d, J=5.7 Hz, 1H), 4.34 (s, 2H), 3.57 (s, 3H), 3.44 (s, 3H), 2.84 (s, 3H). MS (ESI) m/z=557 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-61dd692845d64a5ab75708511bb45749
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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