Sodium hydride → HCID 178432355, compound

HRID 1898453Notes

Reaction equation

HRID 1898453 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]([F:43])([F:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][NH2:41].[H-].[Na+]>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:41][CH2:40][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[C:33]([F:32])([F:42])[F:43])=[O:24])=[CH:13][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 764472-(Trifluoromethyl)benzylamineHCID 178432356HCID 178432356, compound

Product 1

HCID 178432355HCID 178432355, compoundYield 38.3%

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, 0.050 g, 0.132 mmol), oxalyl chloride (0.1 mL), 1-[2-(trifluoromethyl)phenyl]methanamine (0.046 g, 0.262 mmol), THF (5.0 mL) and 60% NaH (0.021 g, 0.525 mmol). The obtained crude product was purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH:DCM to afford 0.027 g of the desired product. 1HNMR (DMSO-d6): δ 2.64 (s, 3H), 4.76 (s, 2H), 7.37-7.47 (m, 2H), 7.61-7.63 (m, 5H), 7.75 (d, J=6.9 Hz, 1H), 8.65 (s, 1H), 9.43 (s, 1H), 11.53 (s, 1H); MS [M+H]+: 534.43.

Workup

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

Sources & evidence

ORD record
ord-3e13a9f312174007929df0c9f83dc8fe
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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