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Oxalyl chloride → HCID 178432347, compound

HRID 1898455
Notes
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Reaction equation

HRID 1898455 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.C(Cl)(=O)C(Cl)=O.[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([CH3:43])([CH3:42])[C:40]#[N:41])=[CH:35][CH:34]=1.CCN(C(C)C)C(C)C>C1COCC1>[C:40]([C:39]([C:36]1[CH:35]=[CH:34][C:33]([NH:32][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])=[CH:38][CH:37]=1)([CH3:43])[CH3:42])#[N:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 100578012-(4-Aminophenyl)-2-methylpropanenitrileHCID 178432356HCID 178432356, compound

Product 1

HCID 178432347HCID 178432347, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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), 2-(4-aminophenyl)-2-methylpropanenitrile (Intermediate-22, 0.063 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 0.012 g of the desired product. 1HNMR (DMSO-d6): δ 1.69 (s, 6H), 2.66 (s, 3H), 7.42 (t, J=7.8 Hz, 1H), 7.51 (d, J=8.7 Hz, 2H), 7.61 (s, 3H), 7.82 (d, J=9.0 Hz, 2H), 9.45 (s, 1H), 10.11 (s, 1H), 11.58 (s, 1H); MS [M+H]+: 519.32.

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-ee08e2a69ec0431cb790b37929be1269
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08519149B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes