1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66835559, compound

HRID 536290Notes

Reaction equation

HRID 536290 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[C:22]([N:26]1[C:39]2[C:38](=[O:40])[CH2:37][C:31]3([CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[CH2:30][C:29]=2[CH:28]=[N:27]1)([CH3:25])([CH3:24])[CH3:23].C(N(C(C)C)CC)(C)C.O.N1(O)C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[C:22]([N:26]1[C:39]2[C:38](=[O:40])[CH2:37][C:31]3([CH2:36][CH2:35][N:34]([C:15]([C:14]4[CH:13]=[CH:12][C:11]([O:10][CH2:9][C:8]5[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:21][CH:20]=5)=[CH:19][CH:18]=4)=[O:17])[CH2:33][CH2:32]3)[CH2:30][C:29]=2[CH:28]=[N:27]1)([CH3:25])([CH3:23])[CH3:24]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 25704163HCID 25704163, compoundHCID 58252518HCID 58252518, compound

Product 1

HCID 66835559HCID 66835559, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-(methoxycarbonyl)benzyloxy)benzoic acid (25 mg, 0.087 mmol), 1-tert-butyl-4,6-dihydrospiro[indazole-5,4′-piperidin]-7(1H)-one (26 mg, 0.087 mmol), diisopropylethylamine (53 μL, 0.30 mmol), 1,2,3-benzotriazole-1-ol, monohydrate (14 mg, 0.087 mmol), 4-dimethylaminopyridine (1.1 mg, 0.01 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (19 mg, 0.96 mmol) in dichloromethane (0.2 mL) was heated at 30° C. for 18 hr. The reaction mixture was partitioned between ethyl acetate/aqueous 0.3N hydrochloric acid, the organic phase was dried over sodium sulfate, concentrated in vacuo and purified by preparative HPLC to afford methyl 4-((4-(1-tert-butyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-ylcarbonyl)phenoxy)methyl)benzoate. HPLC column: Waters Atlantis C18 4.6×50 mm, 5 um, solvent: acetonitrile:water (0.05% TFA); flow rate 2 mL/min; gradient (% organic) start=5%, end=95%, gradient time=4 min, retention time=3.68 min; m/z=530 (M+1).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate/aqueous 0.3N hydrochloric acid
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-98a34cd6426a4d2593ab19d74bbf6436
Source dataset
uspto-grants-2014_10
Patent number
US08859577B2

Reaction notes

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