Toluene → HCID 178521837, compound

HRID 1410234Notes

Reaction equation

HRID 1410234 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[NH:19][C:20]1[NH:24][C:23]2[CH:25]=[C:26]([O:34][CH2:35][CH:36]([F:38])[F:37])[C:27]([C:29]([O:31]CC)=O)=[CH:28][C:22]=2[N:21]=1.[Br:39][C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=1.C[Al](C)C.C1(C)C=CC=CC=1>O1CCOCC1>[Br:39][C:40]1[CH:46]=[CH:45][C:43]([NH:44][C:29]([C:27]2[C:26]([O:34][CH2:35][CH:36]([F:37])[F:38])=[CH:25][C:23]3[NH:24][C:20]([NH:19][C:3]4[CH:4]=[C:5]([CH2:8][NH:9][C:10]([C:12]5([C:15]([F:18])([F:17])[F:16])[CH2:13][CH2:14]5)=[O:11])[CH:6]=[CH:7][C:2]=4[Cl:1])=[N:21][C:22]=3[CH:28]=2)=[O:31])=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 78074-BromoanilineHCID 16682925TrimethylaluminumHCID 178468552HCID 178468552, compound

Product 1

HCID 178521837HCID 178521837, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared in accordance with Example 59 (i) using ethyl 2-(2-chloro-5-{[(1-trifluoromethyl-cyclopropanecarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1H-benzimidazole-5-carboxylate (0.200 g; 0.36 mmol), 4-bromoaniline (0.184 g; 1.07 mmol), Me3Al in toluene (0.900 mL; 2 M; 1.80 mmol) and 1,4-dioxane (10 mL). Yield: 0.115 g (47%). 400 MHz 1H-NMR (DMSO-d6, ppm) 11.3-11.1 (1H, br s) 10.17 (1H, s) 9.1-8.8 (1H, br s) 8.65-8.57 (1H, m) 8.53 (1H, t, J=5.8 Hz) 7.95-7.90 (1H, m) 7.80-7.73 (2H, m) 7.63-7.57 (2H, m) 7.49 (1H, d, J=8.4 Hz) 7.31-7.26 (1H, m) 6.94 (1H, dd, J=8.2, 1.6 Hz) 6.59 (1H, tt, J=54.3, 3.1 Hz) 4.57 (2H, td, J=14.9, 3.0 Hz) 4.38 (2H, d, J=5.8 Hz) 1.54-1.47 (2H, m) 1.38-1.31 (2H, m). MS m/z: 686, 688, 690 [M+H]+.

Sources & evidence

ORD record
ord-10833f1eb9fd4f00a3987196ef0efa59
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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