Sodium cyanoborohydride → 1-(1,3-Dimethyl-1H-pyrazol-4-yl)-N-((1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfinyl)-1H-imidazol-5-yl)methyl)-N-methylmethanamine

HRID 2368534Notes

Reaction equation

HRID 2368534 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]=O)=[CH:11][N:10]=[C:9]2[S:15]([CH2:17][C:18]2[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=2[F:26])=[O:16])=[CH:4][CH:3]=1.[CH3:27][N:28]1[CH:32]=[C:31]([CH2:33][NH:34][CH3:35])[C:30]([CH3:36])=[N:29]1.C([BH3-])#N.[Na+]>CN(C=O)C.C(O)(=O)C>[CH3:27][N:28]1[CH:32]=[C:31]([CH2:33][N:34]([CH2:13][C:12]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:9]([S:15]([CH2:17][C:18]3[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=3[F:26])=[O:16])=[N:10][CH:11]=2)[CH3:35])[C:30]([CH3:36])=[N:29]1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 70102001-(1,3-dimethyl-1H-pyrazol-4-yl)-N-methylmethanamineHCID 711176801-(4-Fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfinyl)-1H-imidazole-5-carbaldehyde

Product 1

HCID 711191801-(1,3-Dimethyl-1H-pyrazol-4-yl)-N-((1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfinyl)-1H-imidazol-5-yl)methyl)-N-methylmethanamine

Reagents, catalysts & solvents 1

HCID 21926011acetic acid N,N-dimethylformamideSolvent

Procedure

A solution of 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfinyl)-1H-imidazole-5-carbaldehyde (33) (39 mg, 0.10 mmol), 1-(1,3-dimethyl-1H-pyrazol-4-yl)-N-methylmethanamine (15 mg, 0.11 mmol), sodium cyanoborohydride (30 mg, 0.11 mmol) and DMF/acetic acid (10/1, 1 mL) was stirred at room temperature overnight. The reaction mixture was directly loaded on to reverse phase preparative HPLC column and purified to yield 1-(1,3-dimethyl-1H-pyrazol-4-yl)-N-((1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfinyl)-1H-imidazol-5-yl)methyl)-N-methylmethanamine (501). 1H NMR (400 MHz, CDCl3) δ: 7.63 (s, 1H), 7.52 (s, 1H), 7.45-7.36 (m, 1H), 7.24-7.09 (m, 4H), 6.90-6.85 (m, 1H), 4.87 (d, J=13.0, 1H), 4.58 (d, J=13.0, 1H), 4.27 (d, J=14.5, 1H), 4.11 (s, 1H), 3.99 (d, J=13.2, 1H), 3.90-3.79 (m, 4H), 2.57 (s, 3H), 2.18 (s, 3H). LC-MS ESI m/z; found 506.2 [M+H]+.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-cbd4e609f2184d6c86e2f47b3659a3cf
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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