Diisopropylethylamine → HCID 69507835, compound

HRID 1374549Notes

Reaction equation

HRID 1374549 reaction equation
OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.Cl.[NH2:33][CH:34]1[C:40](=[O:41])[N:39]([CH3:42])[C:38]2[CH:43]=[CH:44][CH:45]=[CH:46][C:37]=2[C:36]2[CH:47]=[CH:48][CH:49]=[CH:50][C:35]1=2.[C:51](O)(=[O:55])[C@H:52]([CH3:54])[OH:53]>C1COCC1>[OH:53][C@@H:52]([CH3:54])[C:51]([NH:33][CH:34]1[C:40](=[O:41])[N:39]([CH3:42])[C:38]2[CH:43]=[CH:44][CH:45]=[CH:46][C:37]=2[C:36]2[CH:47]=[CH:48][CH:49]=[CH:50][C:35]1=2)=[O:55]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 107689L-Lactic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21076586HCID 21076586, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 69507835HCID 69507835, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydroxybenzotriazole (344 mg, 2.55 mmol), diisopropylethylamine (659 mg, 5.1 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (488 mg, 2.55 mmol) were added to a cooled (0° C.) solution of 7-amino-5-methyl-5H,7H-dibenzo[b,d]azepin-6-one hydrochloride (700 mg, 2.55 mmol) and L-(+)-lactic acid (252 mg, 2.8 mmol) in THF (7 ml) and stirred overnight at r.t. The solvent was evaporated, the residue was taken up in dichloromethane and washed with water. The organic phase was dried over Na2SO4 and evaporated. Upon chromatographic purification (silica gel, dichloromethane/methanol=1:0−9:1) the title compound (820 mg, quant.) was obtained as a white solid.

Workup

  1. customThe solvent was evaporated
  2. washwashed with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated
  5. customUpon chromatographic purification (silica gel, dichloromethane/methanol=1:0−9:1) the title compound (820 mg, quant.)
  6. customwas obtained as a white solid

Sources & evidence

ORD record
ord-0192c99fe501475e868aaad846e1d3fc
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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