Methanol → HCID 86624703, compound

HRID 604918Notes

Reaction equation

HRID 604918 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([NH:22][C:23]2[S:24][C:25]([CH:28]=O)=[CH:26][N:27]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1.O1CCCC1.CO>C(Cl)Cl>[CH:1]1([NH:7][CH2:28][C:25]2[S:24][C:23]([NH:22][C:12]3[CH:13]=[CH:14][C:15]([N:16]4[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]4)=[C:10]([O:9][CH3:8])[CH:11]=3)=[N:27][CH:26]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 7965CyclohexylamineHCID 8028TetrahydrofuranHCID 86624700HCID 86624700, compound

Product 1

HCID 86624703HCID 86624703, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in analogy to example 57 from 19 mg (0.19 mmol) cyclohexylamine and 65 mg (0.21 mmol) 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazole-5-carbaldehyde using a solvent mixture of tetrahydrofurane (1 ml), methanol (1 ml) and methylene chloride (1 ml). The reaction was not complete and the same amount of reagent was added like in example 57. Only the imine was formed. Therefore the crude product was dissolved in methanol (1 ml) and 8.6 mg sodium borohydride was added and the reaction stirred for 4 hours at room temperature. After workup the crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 16 mg (21%) of (5-cyclohexylaminomethyl-thiazol-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a yellow oil. MS ISP (m/e): 398.3 (100) (M+H)+. 1H NMR (CDCl3, 250 MHz): δ (ppm)=7.62 (s, 1H), 7.25 (s, 1H), 7.16 (d, 1H), 7.10 (s, 1H), 6.96 (d, 1H), 6.87 (s, 1H), 3.94 (s, 2H), 3.85 (s, 3H), 2.54 (m, 1H), 2.30 (s, 3H), 1.93 (m, 2H), 1.72 (m, 2H), 1.64 (m, 1H), 1.28-1.09 (m, 5H).

Workup

  1. additionthe same amount of reagent was added like in example 57

Sources & evidence

ORD record
ord-291747e06e2c4ca4b88a5e997ae8f3b9
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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