Oxalyl chloride → HCID 56963371, compound

HRID 931420Notes

Reaction equation

HRID 931420 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].[N:33]1[CH:38]=[CH:37][N:36]=[CH:35][C:34]=1[CH2:39][NH2:40]>>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:40][CH2:39][C:34]3[CH:35]=[N:36][CH:37]=[CH:38][N:33]=3)=[O:18])=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:22][S:23]([C:26]1[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=1)(=[O:25])=[O:24]

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 266781(Pyrazin-2-yl)methanamineHCID 532133574-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoic Acid

Product 1

HCID 56963371HCID 56963371, compoundYield 74%

Procedure

Reaction of oxalyl chloride (74 λL, 0.8 mmol) and benzoic acid 4 (209 mg, 0.6 mmol) with subsequent coupling to 2-pyrazinylmethylamine (90 mg, 0.6 mmol) gave benzamide 13 (192 mg, 74%) as a white powder: mp (EtOAc) 204-206° C.; 1H NMR δ 9.30 (t, J=5.8 Hz, 1H, CONH), 8.66 (d, J=1.5 Hz, 1H, H-3′), 8.59 (dd, J=2.6, 1.5 Hz, 1H, H-5′), 8.54 (d, J=2.6 Hz, 1H, H-6′), 8.02 (d, J=8.6 Hz, 2H, H-2, H-6), 7.90 (d, J=8.6 Hz, 2H, H-3, H-5), 7.67 (d, J=8.3 Hz, 2H, H-2″, H-6″), 7.42 (d, J=8.3 Hz, 2H, H-3″, H-5″), 4.62-4.66 (m, 4H, CH2SO2, CH2N), 2.41 (s, 3H, CH3), 2.14 (s, 3H, CH3); 13C NMR δ 165.7, 158.0, 154.1, 149.9, 144.5, 143.9, 143.5, 143.2, 135.6, 135.3, 129.7 (2), 128.9, 128.3 (2), 128.1 (2), 126.0, 125.4 (2), 53.0, 42.9, 21.0, 9.7; MS m/z 433.6 (MH+, 100%). Anal. calcd for C24H22N4O4S: C, 62.32; H, 4.79; N, 12.11. Found: C, 62.36; H, 4.67; N, 12.09%.

Sources & evidence

ORD record
ord-c8ebde5e6b284780835403accde16224
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

Loading…