Oxalyl chloride → HCID 178432352, compound

HRID 1898454Notes

Reaction equation

HRID 1898454 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23](O)=[O:24])=[CH:13][C:12]=2[N:11]=1.C(Cl)(=O)C(Cl)=O.[F:32][C:33]1([F:40])[CH2:38][CH2:37][CH:36]([NH2:39])[CH2:35][CH2:34]1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([NH:39][CH:36]3[CH2:37][CH2:38][C:33]([F:40])([F:32])[CH2:34][CH2:35]3)=[O:24])=[CH:13][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 3847030(4,4-Difluorocyclohexyl)amineHCID 178432356HCID 178432356, compound

Product 1

HCID 178432352HCID 178432352, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure described for Example-177 using 7-[(2,6-dichlorophenyl)amino]-2-methyl-8H-imidazo[4,5-e][1,3]benzoxazole-4-carboxylic acid (Intermediate-55, 0.100 g, 0.265 mmol), oxalyl chloride (0.2 mL), 4,4-difluorocyclohexanamine (0.069 g, 0.397 mmol), THF (5.0 mL), DIPEA (0.103 g, 0.795 mmol) and TEA (0.2 mL). The obtained crude product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH:DCM to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.66-1.68 (m, 2H), 1.90-2.15 (m, 6H), 2.60 (s, 3H), 4.01 (s, 1H), 7.36 (m, 1H), 7.50 (s, 1H), 7.58 (d, J=7.2 Hz, 2H), 7.89 (s, 1H), 9.38 (s, 1H), 11.46 (s, 1H); MS [M+H]+: 494.41.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude product
  3. customwas further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH

Sources & evidence

ORD record
ord-e86d30bf4c844389bfdcbf04fd28458f
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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