Oxalyl chloride → N-[(1-Methyl-1H-imidazol-2-yl)methyl]-4-(5-methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzamide

HRID 1526812Notes

Reaction equation

HRID 1526812 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24].[CH3:33][N:34]1[CH:38]=[CH:37][N:36]=[C:35]1[CH2:39][NH2:40]>>[CH3:33][N:34]1[CH:38]=[CH:37][N:36]=[C:35]1[CH2:39][NH:40][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([C:11]2[O:12][C:8]([CH3:7])=[C:9]([CH2:22][S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)(=[O:24])=[O:25])[N:10]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 533842(1-methyl-1H-imidazol-2-yl)methanamineHCID 532133574-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoic Acid

Product 1

HCID 56963455N-[(1-Methyl-1H-imidazol-2-yl)methyl]-4-(5-methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzamideYield 70%

Procedure

Reaction of oxalyl chloride (75 λL, 0.86 mmol) and benzoic acid 4 (212 mg, 0.57 mmol) with subsequent coupling to (1-methyl-1H-imidazol-2-yl)methylamine (70 mg, 0.63 mmol) gave benzamide 14 (185 mg, 70%) as a white powder: mp (EtOAc) 190-192° C.; 1H NMR δ 9.05 (t, J=5.5Hz, 1 H, CONH), 8.00 (dd, J=8.6, 1.8Hz, 2 H, H-2, H-6), 7.87 (dd, J=8.6, 1.8Hz, 2H, H-3, H-5), 7.67 (d, J=8.3Hz, 2 H, H-2′, H-6′), 7.42 (d, J=8.3Hz, 2 H, H-3′, H-5′), 7.08 (d, J=1.1Hz, 1 H, H-5″), 6.80 (d, J=1.1Hz, 1 H, H-4″), 4.62 (s, 2 H, CH2SO2), 4.54 (d, J=5.5 Hz, 2 H, CH2N), 3.66 (s, 3 H, NCH3), 2.40 (s, 3 H, CH3), 2.13 (s, 3 H, CH3); 13C NMR δ 165.2, 158.0, 149.9, 144.5 (2), 135.6, 135.3, 129.6 (2), 128.8, 128.3 (2), 128.2 (2), 126.4, 126.0, 125.3 (2), 121.8, 53.0, 35.5, 32.4, 21.0, 9.6; MS m/z 462.5 (MH+, 100%). Anal. calcd for C24H24N4O4S: C, 62.05; H, 5.21; N, 12.06. Found: C, 61.76; H, 5.09; N, 11.76%.

Sources & evidence

ORD record
ord-5f25dbb6bdf84f7f9fb74775b990e302
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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