2-Methoxyethylamine → HCID 44556155, compound

HRID 336403Notes

Reaction equation

HRID 336403 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]3[N:15]=[C:16]([NH:18][C:19]4[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=4)[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:27][O:28][CH2:29][CH2:30][NH2:31].C([BH3-])#N.[Na+]>O1CCCC1>[CH3:27][O:28][CH2:29][CH2:30][NH:31][CH2:23][C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:16]2[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[N:14]3[N:15]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 5003444Sodium cyanoborohydrideHCID 59186519HCID 59186519, compound

Product 1

HCID 44556155HCID 44556155, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzaldehyde (47 mg, 0.14 mmol) and 2-methoxyethylamine (65 μL, 0.70 mmol) and 4 Å molecular sieves in tetrahydrofuran (5 mL) was stirred at 24° C. After 18 h, sodium cyanoborohydride (100 mg, 2 mmol) was added to the reaction mixture. After 1 h, the reaction mixture was partitioned between ethyl acetate (20 mL) and water (10 mL). The organic was separated and washed with saturated aqueous sodium chloride solution (10 mL). The collected organic was dried over magnesium sulfate, filtered, and concentrated. Purification by preparative HPLC provided a tan solid (18.6 mg, 34%). LCMS (ESI) m/z: 404. 1H NMR (400 MHz, DMSO-d6), δ: 9.51 (s, 1H), 8.05 (d, J=8.8, 2 H), 7.62 (m, 3H), 7.52 (d, J=8.7, 1H), 7.20 (d, J=8.4, 2H), 7.16-7.10 (m, 3H), 3.87 (s, 3H), 3.62 (s, 2H), 3.39 (t, J=5.7, 2H), 3.23 (s, 3H), 3.17 (d, J=5.2, 2H), 2.63 (t, J=5.7, 2H).

Workup

  1. waitAfter 1 h
  2. customthe reaction mixture was partitioned between ethyl acetate (20 mL) and water (10 mL)
  3. customThe organic was separated
  4. washwashed with saturated aqueous sodium chloride solution (10 mL)
  5. dry with materialThe collected organic was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-33c1e466b89a424fb0cc71cee734aac0
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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