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Acetic Acid → 2-{3-Methoxy-6-[3-methoxy-5-methylaminomethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester

HRID 2234140
Notes
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Reaction equation

HRID 2234140 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])=[C:25]([CH:40]=O)[CH:24]=2)[N:20]=[N:19][C:18]=1[O:42][CH3:43])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN.C(O)(=O)C.[C:50]([BH3-])#[N:51].[Na+]>CO.C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([C:23]2[CH:24]=[C:25]([CH2:40][NH:51][CH3:50])[C:26]([O:31][CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])=[C:27]([O:29][CH3:30])[CH:28]=2)[N:20]=[N:19][C:18]=1[O:42][CH3:43])=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 866120602-{6-[3-Formyl-5-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-3-methoxy-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 68638496
2-{3-Methoxy-6-[3-methoxy-5-methylaminomethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

175 mg of 2-{6-[3-Formyl-5-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-3-methoxy-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester is dissolved in 5 ml of methanol and 0.16 ml of methylamine solution in THF is added. The solution is stirred for 10 min at RT then 19 mg of acetic acid and 20 mg of sodium cyanoborohydride is added. The reaction is stirred for 20 h at RT. The product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). Yield 118 mg. LC-MS (ES+) 621 (M+H)+.

Workup

  1. stirringThe reaction is stirred for 20 h at RT
  2. customThe product is purified by preparative RP-HPLC
  3. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)

Sources & evidence

ORD record
ord-17776915ea6546738f158c03ffed3104
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709466B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes