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Formaldehyde → Methyl 4-cyclobutyl-2-methyl-5-(6-methyl-1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepin-2-yl)benzoate

HRID 1487956
Notes
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Reaction equation

HRID 1487956 reaction equation
Cl.[CH:2]1([C:6]2[C:15]([C:16]3[NH:25][C:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:18]=4[N:17]=3)=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([CH3:26])[CH:7]=2)[CH2:5][CH2:4][CH2:3]1.[BH-](OC(C)=O)(OC(C)=O)O[C:29](C)=O.[Na+].C=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH:2]1([C:6]2[C:15]([C:16]3[NH:17][C:18]4[CH2:24][CH2:23][N:22]([CH3:29])[CH2:21][CH2:20][C:19]=4[N:25]=3)=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([CH3:26])[CH:7]=2)[CH2:3][CH2:4][CH2:5]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 118250742Methyl 4-cyclobutyl-5-(1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepin-2-yl)-2-methylbenzoate hydrochloride2×

Product 1

HCID 90066723Methyl 4-cyclobutyl-2-methyl-5-(6-methyl-1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepin-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Into a 100-mL round-bottom flask, was placed a mixture of methyl 4-cyclobutyl-5-(1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepin-2-yl)-2-methylbenzoate hydrochloride (compound 82.7, 40 mg, 0.11 mmol), NaBH(OAc)3 (75 mg, 0.35 mmol), and formaldehyde (37 wt %) (26 μL, 0.33 mmol) in tetrahydrofuran (4 mL). The resulting mixture was stirred for 2 h at 40° C., then cooled and the pH of the solution was adjusted to 8-9 with sodium bicarbonate (sat.). The aqueous phase was extracted with ethyl acetate (2×20 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to yield 20 mg (crude) of the title compound as a yellow solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. temperaturecooled
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×20 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f19a4ce641de436ca5cd4856f67c95cc
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428502B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes