Phenol → HCID 24786069, compound

HRID 2239349Notes

Reaction equation

HRID 2239349 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([O:15]C)=O)=[C:10](/[N:17]=[CH:18]/[N:19]([CH3:21])C)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][CH:26]([O:29][C:30]2[CH:35]=[C:34](CN)[CH:33]=[CH:32][N:31]=2)[CH2:25][CH2:24]1.C1(O)C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]3[C:13](=[O:15])[N:19]([CH2:21][C:34]4[CH:33]=[CH:32][N:31]=[C:30]([O:29][CH:26]5[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]5)[CH:35]=4)[CH:18]=[N:17][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 21959563HCID 21959563, compoundHCID 178499302HCID 178499302, compound

Product 1

HCID 24786069HCID 24786069, compound

Conditions

Temperature
120 °C

Procedure

Methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (0.388 g, 1.20 mmol) and 1-{2-[(1-methylpiperidin-4-yl)oxy]pyridin-4-yl}methanamine (0.242 g, 1.09 mmol, from step b above) were mixed with 1.0 g of phenol and heated to 120° C. for 2 h. The mixture was purified by preparative HPLC (Kromasil C8-50×250 mm, CH3CN/0, 1 M NH4OAc 5/95-50/50 and CH3CN/0, 2% HOAc 5/95-50/50). The product was freeze dried from water. Yield: 0.154 g (27%). 1H NMR (400 MHz, DMSO-d6) δ 8.63 (s, 1H), 8.09 (d, 1H), 7.94 (s, 1H), 7.90 (m, 2H), 7.58 (m, 2H), 6.88 (m, 1H), 6.60 (bs, 1H), 5.20 (s, 2H), 4.95 (m, 1H), 2.60 (m, 2H), 2.15 (s, 3H), 2.12 (m, 2H), 1.92 (m, 2H), 1.62 (m, 2H). 13C NMR (100 MHz, DMSO-d6) δ 163.7, 158.6, 156.8, 150.6, 149.4, 147.9, 135.1, 131.9, 130.0, 128.7, 122.5, 122.4, 116.1, 109.7, 53.4, 48.5, 46.5, 31.3. MS (ESI+) 467/469 (M+1H+).

Workup

  1. customThe mixture was purified by preparative HPLC (Kromasil C8-50×250 mm, CH3CN/0, 1 M NH4OAc 5/95-50/50 and CH3CN/0, 2% HOAc 5/95-50/50)
  2. dry with materialdried from water

Sources & evidence

ORD record
ord-11213d0dfd4d4f688388d9b44bd2be9b
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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