Diisopropylethylamine → HCID 69507675, compound

HRID 1374553Notes

Reaction equation

HRID 1374553 reaction equation
O[C:2]1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.[NH2:32][C@@H:33]1[C:39](=[O:40])[N:38]([CH:41]2[CH2:43][CH2:42]2)[C:37]2[CH:44]=[CH:45][CH:46]=[CH:47][C:36]=2[N:35]([CH3:48])[CH2:34]1.[C:49]([OH:54])(=O)[C@H:50]([CH3:52])[OH:51]>C1COCC1>[CH:43]1([CH2:41][N:38]2[C:39](=[O:40])[C@@H:33]([NH:32][C:49](=[O:54])[C@@H:50]([OH:51])[CH3:52])[CH2:34][N:35]([CH3:48])[C:36]3[CH:47]=[CH:46][CH:45]=[CH:44][C:37]2=3)[CH2:42][CH2:2]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 107689L-Lactic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69507494HCID 69507494, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 69507675HCID 69507675, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydroxybenzotriazole (121 mg, 1 mmol), diisopropylethylamine (23 2 mg, 2 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (172 mg, 1 mmol) were added to a cooled (0° C.) solution of (S)-3-amino-1-cyclopropyl-5-methyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one (220 mg, 1 mmol) and L-(+)-lactic acid (81 mg, 1 mmol) in THF (2 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 (347 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 (347 mg, quant.)
  6. customwas obtained as a white solid

Sources & evidence

ORD record
ord-cc22f71021d94a0cbed3c6cbbbe8695b
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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