Dimethylamine, hydrochloride → HCID 67278895, compound

HRID 1693379Notes

Reaction equation

HRID 1693379 reaction equation
C(OC([NH:8][C@@H:9]([CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C:10]([OH:12])=O)=O)(C)(C)C.[ClH:20].[CH3:21][NH:22][CH3:23].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[ClH:20].[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C:10]([N:22]([CH3:23])[CH3:21])=[O:12]

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7020919Boc-3-(3-pyridyl)-Ala-OH

Product 1

HCID 67278895HCID 67278895, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2-tert-butoxycarbonylamino-3-pyridin-3-ylpropionic acid (500 mg, 1.88 mmol) in DMF (10 mL) was added dimethylamine hydrochloride (153 mg, 1.88 mmol), DIPEA (1.2 mL, 6.57 mmol) and TBTU (602 mg, 1.88 mol). The reaction mixture was stirred at rt for 16 h. The solvent was removed in vacuo and the residue dissolved in methanol (20 mL). To this was added 4M hydrochloric acid in dioxane (20 mL) and the reaction was stirred for 16 h at rt. The solvent was removed in vacuo and the residue was partitioned between water (100 mL) and ethyl acetate (2×100 mL). The aqueous layer was evaporated to dryness and the residue recrystallised from ethanol/ethoxyethanol (9:1), to give the title compound as a white solid. δH (CD3OD): 2.99 (3H, s), 3.06 (3H, s), 3.35-3.42 (1H, m), 3.45-3.53 (1H, m), 4.87-4.94 (1H, m), 8.04-8.10 (1H, m), 8.48-8.53 (1H, m), 8.84-8.90 (2H, m).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in methanol (20 mL)
  3. additionTo this was added 4M hydrochloric acid in dioxane (20 mL)
  4. stirringthe reaction was stirred for 16 h at rt
  5. customThe solvent was removed in vacuo
  6. customthe residue was partitioned between water (100 mL) and ethyl acetate (2×100 mL)
  7. customThe aqueous layer was evaporated to dryness
  8. customthe residue recrystallised from ethanol/ethoxyethanol (9:1)

Sources & evidence

ORD record
ord-0c6632b09d474a9596908c724535b001
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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