1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68355427, compound

HRID 886453Notes

Reaction equation

HRID 886453 reaction equation
[Li+].[CH:2]([N:5]1[C:9]([C:10]2[N:19]=[C:18]3[N:12]([CH2:13][CH2:14][O:15][C:16]4[CH:23]=[C:22]([NH:24][CH2:25][C:26]([O-])=[O:27])[CH:21]=[CH:20][C:17]=43)[CH:11]=2)=[N:8][CH:7]=[N:6]1)([CH3:4])[CH3:3].C([N:31]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[Cl-].[NH4+]>CN(C=O)C>[CH:2]([N:5]1[C:9]([C:10]2[N:19]=[C:18]3[C:17]4[CH:20]=[CH:21][C:22]([NH:24][CH2:25][C:26]([NH2:31])=[O:27])=[CH:23][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:11]=2)=[N:8][CH:7]=[N:6]1)([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 67050783HCID 67050783, compound

Product 1

HCID 68355427HCID 68355427, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-ylamino]-acetic acid lithium salt (130 mg, 0.35 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (82 mg, 0.42 mmol), 1-hydroxybenzotriazole hydrate (55 mg, 0.42 mmol) and DIPEA (0.42 mL, 1.4 mmol) in DMF (2 mL) was stirred at RT for 5 min before ammonium chloride (55 mg, 1.05 mmol) was added and the reaction stirred at RT for 18 h. The mixture was concentrated in vacuo and the resultant residue triturated with water. The solid was filtered off, washed with water then dried in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 10% methanol in DCM) to give 444 (48 mg, 37%). LCMS: RT=2.10 min, [M+H]+=368. 1H NMR 400 MHz (DMSO-d6) δ: 8.12 (1H, d, J=8.80 Hz), 7.88 (1H, d, J=0.63 Hz), 7.77 (1H, s), 7.37 (1H, br, s), 7.11 (1H, br, s), 6.45 (1H, dd, J=8.84, 2.36 Hz), 6.32 (1H, br, t), 6.10 (1H, d, J=2.33 Hz), 5.92 (1H, m), 4.42 (4H, m), 3.63 (2H, d, J=5.84 Hz), 1.47 (6H, d, J=6.60 Hz)

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe resultant residue triturated with water
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customthen dried in vacuo

Sources & evidence

ORD record
ord-c65857126cce4c7dbc968be36bb4dcec
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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