Thionyl Chloride → HCID 178422736, compound

HRID 1898425Notes

Reaction equation

HRID 1898425 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.[CH:31]1([C:34]2[CH:35]=[CH:36][C:37]([F:41])=[C:38]([CH:40]=2)[NH2:39])[CH2:33][CH2:32]1.CCN(C(C)C)C(C)C>C1COCC1>[CH:31]1([C:34]2[CH:35]=[CH:36][C:37]([F:41])=[C:38]([NH:39][C:24]([C:16]3[C:17]4[O:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]=4[C:12]4[NH:11][C:10]([NH:9][C:3]5[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=5[Cl:8])=[N:14][C:13]=4[CH:15]=3)=[O:25])[CH:40]=2)[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 675036775-Cyclopropyl-2-fluoroanilineHCID 178422813HCID 178422813, compound

Product 1

HCID 178422736HCID 178422736, compoundYield 14.9%

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, 0.100 g, 0.255 mmol), thionyl chloride (1.0 mL), 5-cyclopropyl-2-fluoro aniline (Intermediate-47, 0.077 g, 0.511 mmol), THF (5.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on neutral alumina eluting with 1.0-2.0% MeOH:DCM to afford 0.020 g of the desired product 1HNMR (DMSO-d6): δ 0.62 (m 2H), 0.94 (d, J=6.3 Hz, 2H), 1.54 (s, 6H), 1.93 (m, 1H), 3.11 (s, 2H), 6.80 (m, 1H), 7.17 (m, 2H), 7.54 (m, 3H), 8.22 (s, 1H), 10.04 (s, 1H), 11-11.5 (s, 2H); MS [M]+: 525.15.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude product
  3. customwas purified by column chromatography on neutral alumina eluting with 1.0-2.0% MeOH

Sources & evidence

ORD record
ord-cf19741e78ad48caa289661ccb4bac82
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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