Thionyl Chloride → HCID 178422747, compound

HRID 1898431Notes

Reaction equation

HRID 1898431 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F: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]([OH:26])=O)=[CH:15][C:13]=2[N:14]=1.S(Cl)(Cl)=O.[CH:31]1([C:34]2[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=2)[NH2:37])[CH2:33][CH2:32]1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:22])([CH3:23])[O:21][C:17]=3[C:16]([C:24]([NH:37][C:36]3[CH:38]=[CH:39][CH:40]=[C:34]([CH:31]4[CH2:33][CH2:32]4)[CH:35]=3)=[O:26])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 120321393-CyclopropylanilineHCID 178422815HCID 178422815, compound

Product 1

HCID 178422747HCID 178422747, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the same procedure as described for Example-108 using 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.150 g, 0.400 mmol), thionyl chloride (2.0 mL), 3-cyclopropyl aniline (0.079 g, 0.598 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 0.070 g of the desired product. 1HNMR (DMSO-d6): δ 0.66 (d, J=4.8 Hz, 2H), 0.93 (d, J=2.1 Hz, 2H), 1.57 (s, 6H), 1.92 (m, 1H), 3.10 (s, 2H), 6.77 (d, J=7.8 Hz, 1H), 7.18-7.48 (m, 7H), 9.69 (s, 1H), 11.13 (s, 2H); MS [M]+: 491.30.

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-cd6324052f25447ca1110ab1ff7f27ee
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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