Thionyl Chloride → HCID 178426548, compound

HRID 1898408Notes

Reaction equation

HRID 1898408 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:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24](O)=[O:25])=[CH:15][C:13]=2[N:14]=1.S(Cl)(Cl)=O.[F:31][C:32]1[CH:38]=[C:37]([CH3:39])[CH:36]=[CH:35][C:33]=1[NH2:34].CCN(C(C)C)C(C)C>C1COCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([NH:34][C:33]3[CH:35]=[CH:36][C:37]([CH3:39])=[CH:38][C:32]=3[F:31])=[O:25])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 679842-Fluoro-4-methylanilineHCID 81531DiisopropylethylamineHCID 178422813HCID 178422813, compound

Product 1

HCID 178426548HCID 178426548, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure described for Example-108 using 2-[(2,6-dichlorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-6, 0.200 g, 0.512 mmol), thionyl chloride (2.0 mL), 2-fluoro-4-methylaniline (0.128 g, 1.025 mmol), THF (5.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.075 g of the desired product. 1HNMR (DMSO-d6): δ 1.55 (s, 6H), 2.29 (s, 3H), 3.10 (s, 2H), 7.00 (d, J=8.1 Hz, 1H), 7.15 (d, J=12 Hz, 1H), 7.24 (m, 1H), 7.42 (m, 1H), 7.53 (d, J=8.1 Hz, 2H), 8.33 (t, J=8.4 Hz, 1H), 9.99 (s, 1H), 11.00 (s, 2H); MS [M+H]+: 500.39.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude product
  3. customwas purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH

Sources & evidence

ORD record
ord-1e5e5139e88b4c05aae467af7fd05e75
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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