Thionyl Chloride → HCID 178432354, compound

HRID 1898448Notes

Reaction equation

HRID 1898448 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]([OH:25])=O)=[CH:13][C:12]=2[N:11]=1.S(Cl)(Cl)=O.[CH:30]1([CH2:36][NH2:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.CCN(C(C)C)C(C)C>C1COCC1>[CH:30]1([CH2:36][NH:37][C:23]([C:14]2[C:15]3[O:19][C:18]([CH3:20])=[N:17][C:16]=3[C:21]3[NH:22][C:10]([NH:9][C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])=[N:11][C:12]=3[CH:13]=2)=[O:25])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 178432356HCID 178432356, compound

Product 1

HCID 178432354HCID 178432354, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure described for Example-181 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), thionyl chloride (2.0 mL), 1-cyclohexylmethanamine (0.023 g, 0.138 mmol), THF (5.0 mL) and DIPEA (0.086 g, 0.663 mmol). The obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH: DCM to afford 0.020 g of the desired product. 1HNMR (DMSO-d6): δ 1.04-1.31 (m, 6H), 1.62-1.75 (m, 5H), 2.54 (s, 3H), 3.00 (t, J=18.6 Hz, 2H), 7.34 (s, 1H), 7.53-7.59 (m, 3H), 7.94 (s, 1H), 9.39 (s, 1H), 11.51 (s, 1H); MS [M+H]+: 472.43.

Workup

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

Sources & evidence

ORD record
ord-0459a90fb88e41e795b1745e3c518a28
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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