Acetic Acid → HCID 68637619, compound

HRID 2234136Notes

Reaction equation

HRID 2234136 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]([CH:29]=O)[CH:26]=[C:25]([CH:31]=[O:32])[CH:24]=2)[N:20]=[N:19][C:18]=1[O:33][CH3:34])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN.C(O)(=O)C.[C:41]([BH3-])#[N:42].[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:28]=[C:27]([CH2:29][NH:42][CH3:41])[CH:26]=[C:25]([CH2:31][OH:32])[CH:24]=2)[N:20]=[N:19][C:18]=1[O:33][CH3:34])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 86612059HCID 86612059, compound

Product 1

HCID 68637619HCID 68637619, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

170 mg of 2-[6-(3,5-diformyl-phenyl)-3-methoxy-pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester is dissolved in 5 ml of methanol and 0.093 ml of methylamine solution in THF is added. The solution is stirred for 5 min at RT then 22 mg of acetic acid and 26 mg of sodium cyanoborohydride is added. The reaction is stirred for 4 h at 60° C. The product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). Yield 19 mg. LC-MS (ES+) 475 (M+H)+.

Workup

  1. stirringThe reaction is stirred for 4 h at 60° C
  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-5a2a9069ff4343f4a5cdd8600deb1351
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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