Diisopropylethylamine → HCID 66611155, compound

HRID 1812124Notes

Reaction equation

HRID 1812124 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][N:8]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[C:17]([NH:24][C:25]4[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=4)=[N:18][CH:19]=[C:20]([CH:23]=3)[CH:21]=O)[N:10]=2)=[CH:5][CH:4]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[NH:59]1[CH2:62][CH2:61][CH2:60]1.C(N(C(C)C)CC)(C)C>CO.C(Cl)Cl>[N:59]1([CH2:21][C:20]2[CH:23]=[C:16]([C:11]3[N:12]=[C:13]([CH3:15])[N:14]=[C:9]([N:8]([CH2:7][C:6]4[CH:42]=[CH:43][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[CH2:33][C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=4)[N:10]=3)[C:17]([NH:24][C:25]3[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)=[N:18][CH:19]=2)[CH2:62][CH2:61][CH2:60]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 12308726Azetidine hydrochlorideHCID 601552675-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde

Product 1

HCID 66611155HCID 66611155, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (228 mg, 0.395 mmol) and sodium triacetoxyborohydride (125 mg, 0.592 mmol) were added to a solution of azetidine hydrochloride (Aldrich, St. Louis, Mo.) (48.0 mg, 0.513 mmol) in methanol (2 mL), DCM (2 mL) and diisopropylethylamine (103 μL, 0.592 mmol). The reaction mixture was stirred at ambient temperature for 2 h. More sodium triacetoxyborohydride was added and the mixture was allowed to stir at ambient temperature for 30 min. The reaction mixture was concentrated and diluted with 150 mL of DCM, added to a separatory funnel, partitioned with water, washed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous), separated, diluted with a small amount of methanol to make the solution clear, dried over sodium sulfate, and concentrated to give 4-(5-(azetidin-1-ylmethyl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (150 mg, 61.4% yield). m/z (ESI, +ve ion) 619.2 (M+H)+.

Workup

  1. stirringto stir at ambient temperature for 30 min
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with 150 mL of DCM
  4. additionadded to a separatory funnel
  5. custompartitioned with water
  6. washwashed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous)
  7. customseparated
  8. additiondiluted with a small amount of methanol
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f742be65cac841029efc82a07efcf10c
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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