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

HRID 1803267Notes

Reaction equation

HRID 1803267 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[CH2:5]=O.[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](N)[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]([N:2]([CH3:1])[CH3:5])[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

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58110003N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

Product 1

HCID 58110186N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-N6,N6-dimethyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamineYield 52.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (14.53 mg, 0.231 mmol) and formaldehyde (16.15 μL, 0.217 mmol) were added to a solution of N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine (18 mg, 0.038 mmol, from example 78) in MeOH (0.4 mL). The mixture was stirred at rt for 20 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/min, 30-95% B, 20 min to afford 10 mg (47% yield) of the titled compound as a white solid. LC-MS (M+H)+ 498.3.

Workup

  1. customThe crude reaction mixture
  2. customwas purified

Sources & evidence

ORD record
ord-6c1602a873a84243a9b7f8822e7d3563
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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