Thionyl Chloride → HCID 178441027, compound

HRID 1898449Notes

Reaction equation

HRID 1898449 reaction equation
[CH:1]1([C:4]2[O:5][C:6]3[C:12]([C:13]([OH:15])=O)=[CH:11][C:10]4[N:16]=[C:17]([NH:19][C:20]5[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=5[Cl:27])[NH:18][C:9]=4[C:7]=3[N:8]=2)[CH2:3][CH2:2]1.S(Cl)(Cl)=O.[C:32]([C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1)([CH3:35])([CH3:34])[CH3:33].[H-].[Na+]>C1COCC1.C1C=CC=CC=1>[C:32]([C:36]1[CH:37]=[CH:38][C:39]([NH:40][C:13]([C:12]2[C:6]3[O:5][C:4]([CH:1]4[CH2:2][CH2:3]4)=[N:8][C:7]=3[C:9]3[NH:18][C:17]([NH:19][C:20]4[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=4[Cl:27])=[N:16][C:10]=3[CH:11]=2)=[O:15])=[CH:41][CH:42]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 698614-Tert-ButylanilineHCID 178524059HCID 178524059, compound

Product 1

HCID 178441027HCID 178441027, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-177 using 2-cyclopropyl-7-[(2,6-dichlorophenyl)amino]-8H-imidazo[4,5-e][1,3]benzoxazole-4-carboxylic acid (Intermediate-58, 0.100 g, 0.248 mmol), benzene (4 mL), thionyl chloride (5.0 mL), 4-tert-butylaniline (0.055 g, 0.369 mmol), THF (5.0 mL) and 60% NaH (0.095 g, 0.744 mmol). The obtained 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 1.20 (s, 4H), 1.29 (s, 9H), 2.32 (m, 1H), 7.28 (d, J=7.8 Hz, 3H), 7.59 (s, 3H), 7.68 (d, J=8.4 Hz, 2H), 9.36 (s, 1H), 9.90 (s, 1H), 11.55 (s, 1H); MS [M+H]+: 534.32.

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-d76185d330044173b8f7bc21497c0a33
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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