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Triethylamine → 1-Chloro-isoquinoline-5-sulfonic acid {2-[2-(2-trifluoromethyl-phenoxy)-ethylamino]-ethyl}-amide

HRID 2219231
Notes
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Reaction equation

HRID 2219231 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH:7]=O.Cl.[NH2:16][CH2:17][CH2:18][NH:19][S:20]([C:23]1[C:24]2[CH:25]=[CH:26][N:27]=[C:28]([Cl:33])[C:29]=2[CH:30]=[CH:31][CH:32]=1)(=[O:22])=[O:21].CCN(CC)CC.[BH4-].[Na+]>CO>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH2:7][NH:16][CH2:17][CH2:18][NH:19][S:20]([C:23]1[C:24]2[CH:25]=[CH:26][N:27]=[C:28]([Cl:33])[C:29]=2[CH:30]=[CH:31][CH:32]=1)(=[O:21])=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 28338359(2-Trifluoromethyl-phenoxy)-acetaldehydeHCID 866109261-Chloro-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide hydrochloride

Product 1

HCID 866109341-Chloro-isoquinoline-5-sulfonic acid {2-[2-(2-trifluoromethyl-phenoxy)-ethylamino]-ethyl}-amideYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A 4.2 mL of the (2-trifluoromethyl-phenoxy)-acetaldehyde stock solution (˜0.69 mmol) is added to a stirred mixture of 1-chloro-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide hydrochloride (200 mg, 0.621 mmol), 4 Å molecular sieve (400 mg) and NEt3 (0.19 mL, 1.4 mmol) in anhydrous CH3OH (5 mL) at ambient temperature under nitrogen. The resultant mixture is stirred for 16 hours. The mixture is cooled to 0° C. before it is treated with powdered sodium borohydride (53 mg, 1.4 mmol). The mixture is stirred at 0° C. for 1 hour and at ambient temperature for another 1 hour. After filtration and subsequent concentration in vacuo, the crude product is chromatographed on silica (gradient 0-5% CH3OH in CH2Cl2) to give 92 mg (0.19 mmol, 31% yield) of 1-chloro-isoquinoline -5-sulfonic acid {2-[2-(2-trifluoromethyl-phenoxy)-ethylamino]-ethyl}-amide. ESIMS: m/z 474 [(M+H)+, 35Cl], 476 [(M+H)+, 37Cl].

Workup

  1. filtrationAfter filtration and subsequent concentration in vacuo
  2. customthe crude product is chromatographed on silica (gradient 0-5% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-3ae807e264a142d9a2104a02dfc166cf
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07414063B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes