Ammonia → HCID 68775331, compound

HRID 1410464Notes

Reaction equation

HRID 1410464 reaction equation
[K+].[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[O:25][C:24]([C:26]4[CH:34]=[CH:33][CH:32]=[C:31]5[C:27]=4[CH:28]=[CH:29][NH:30]5)=[N:23][C:22]=3[C:35]([O-])=[O:36])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].O.OC1C2N=N[NH:45]C=2C=CC=1.Cl.CN(C)CCCN=C=NCC.N.O1CCOCC1>C(Cl)Cl.CN(C=O)C>[C:35]([C:22]1[N:23]=[C:24]([C:26]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:27]=2[CH:28]=[CH:29][NH:30]3)[O:25][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([N:12]2[CH2:13][CH2:14][N:9]([C:7]([O:6][C:2]([CH3:4])([CH3:5])[CH3:3])=[O:8])[CH2:10][CH2:11]2)=[CH:16][CH:17]=1)(=[O:36])[NH2:45]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68776100HCID 68776100, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 68775331HCID 68775331, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-2-(1H-indol-4-yl)oxazole-4-carboxylic acid potassium salt (0.045, 0.09 mmol) in DCM (0.9 ml) and DMF (0.7 ml) was added hydroxybenzotriazole monohydrate (0.018 g, 0.12 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.027 g, 0.14 mmol) and 0.5M ammonia in dioxane (0.9 m, 0.45 mmol) and the resultant mixture stirred overnight at room temperature. The solvent was then removed in vacuo and the residue purified by preparative HPLC to afford tert-butyl 4-(4-(4-carbamoyl-2-(1H-indol-4-yl)oxazol-5-yl)phenyl)piperazine-1-carboxylate (0.027 g, 0.06 mmol, 65%). LCMS (2) Rt: 3.33 min; m/z (ES+) 488.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-e773f4cd618049ba80bcc01dae3950d3
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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