Methylamine → N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-N6-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

HRID 1803268Notes

Reaction equation

HRID 1803268 reaction equation
[C:1]([BH3-])#[N:2].[Na+].CN.[Cl:7][C:8]1[N:9]=[CH:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[S:21][C:22]4[CH2:28][C:27](=O)[CH2:26][CH:25]([C:30]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=5)[C:23]=4[N:24]=3)=[CH:15][C:14]=2[O:37][CH3:38])[CH:12]=1>CO>[Cl:7][C:8]1[N:9]=[CH:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[S:21][C:22]4[CH2:28][CH:27]([NH:2][CH3:1])[CH2:26][CH:25]([C:30]5[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=5)[C:23]=4[N:24]=3)=[CH:15][C:14]=2[O:37][CH3:38])[CH:12]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 581100012-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-(4-fluorophenyl)-4,5-dihydrobenzo[d]thiazol-6(7H)-one

Product 1

HCID 46864518N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-N6-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamineYield 9.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (37 mg, 0.59 mmol) and methylamine (170 μL, 0.34 mmol) were added to a solution of 2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-(4-fluorophenyl)-4,5-dihydrobenzo[d]thiazol-6(7H)-one (50 mg, 0.107 mmol, from example 75) in MeOH (1.1 mL). The mixture was stirred at rt for 4 hours. The crude reaction mixture was purified using preparatory HPLC (Column: Phenomenex Luna C18 30×100 mm, Solvent A=10 mM Ammonium Acetate in 95:5 water/ACN, Solvent B=10 mM Ammonium Acetate in 5:95 water/ACN. Flow rate: 40 ml/mM, 30-95% B, 20 min to afford 5.0 mg (9% yield) of N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-N6-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine. LC-MS (M+H)+ 484.2.

Workup

  1. customThe crude reaction mixture
  2. customwas purified

Sources & evidence

ORD record
ord-d8746a9b9438470bb5d14cf11abaa9c3
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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