1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57384341, compound

HRID 706672Notes

Reaction equation

HRID 706672 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]([NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][N:22]4[CH2:27][C:28]3[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=3)[C:31](O)=[O:32])=[O:16])=[CH:13][N:14]=[C:8]2[CH:7]=1.C1C=CC2N(O)N=[N:43]C=2C=1.CCN=C=NCCCN(C)C.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[NH4+].[NH4+]>O.CCOCC.C1COCC1>[C:31]([C:30]1[CH:29]=[C:28]([CH:36]=[CH:35][CH:34]=1)[CH2:27][N:22]1[C:23]2[C:19](=[C:18]([NH:17][C:15]([C:12]3[N:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][C:8]4=[N:14][CH:13]=3)=[O:16])[CH:26]=[CH:25][CH:24]=2)[CH:20]=[N:21]1)(=[O:32])[NH2:43]

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 517111Ammonium CarbonateHCID 67976921HCID 67976921, compound

Product 1

HCID 57384341HCID 57384341, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a vial was added 3-((4-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)benzoic acid (0.020 g, 0.0412 mmol), HOBT (0.00612 g, 0.0453 mmol) and EDCI (0.00869 g, 0.0453 mmol) followed by THF (0.500 mL). Diisopropylethylamine (0.00789 mL, 0.0453 mmol) was added and the mixture was stirred for 15 minutes. Ammonium carbonate (0.0119 g, 0.124 mmol) was added in one portion and the mixture was stirred vigorously overnight. The mixture was diluted with water and the resulting precipitate was isolated by vacuum filtration and washed with water. The solid was isolated and slurried in Et2O and filtered and the solid was washed with Et2O and hexanes, then dried under vacuum (0.025 g). The crude solid was purified by preparative TLC (10% MeOH/CH2Cl2) which provided 0.003 g (15%) of the desired product. MS (ES+APCI) m/z=485 (M+H).

Workup

  1. stirringthe mixture was stirred vigorously overnight
  2. customthe resulting precipitate was isolated by vacuum filtration
  3. washwashed with water
  4. customThe solid was isolated
  5. filtrationfiltered
  6. washthe solid was washed with Et2O and hexanes
  7. customdried under vacuum (0.025 g)
  8. customThe crude solid was purified by preparative TLC (10% MeOH/CH2Cl2) which

Sources & evidence

ORD record
ord-795f45cc58fb4b1c8519c336a92b95f4
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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