1,2-Dichloroethane → (4-{N'-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-benzoyl]-hydrazinocarbonyl}-cyclohexyl)-carbamic acid tert-butyl ester

HRID 403516Notes

Reaction equation

HRID 403516 reaction equation
[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([NH:21][NH2:22])=[O:20])=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2].[C:25]([O:29][C:30]([NH:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([C:39](O)=[O:40])[CH2:35][CH2:34]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[C:25]([O:29][C:30](=[O:31])[NH:32][CH:33]1[CH2:34][CH2:35][CH:36]([C:39]([NH:22][NH:21][C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([CH2:14][C:13]3[C:3]([CH2:1][CH3:2])=[N:4][N:5]4[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][C:6]=34)=[CH:24][CH:23]=2)=[O:40])[CH2:37][CH2:38]1)([CH3:28])([CH3:26])[CH3:27]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 68378940HCID 68378940, compoundHCID 178453972HCID 178453972, compound

Product 1

HCID 68379107(4-{N'-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-benzoyl]-hydrazinocarbonyl}-cyclohexyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-benzoic acid hydrazide (29) (200 mg, 0.618 mmol), trans-4-(tert-butoxycarbonylamino) cyclohexanecarboxylic acid (226 mg, 0.928 mmol), EDC (119 mg, 0.618 mmol), HOBT (95 mg, 0.618 mmol) and Et3N (0.086 ml, 0.618 mmol) were dissolved in 2 ml of DMF and stirred for 16 h at rt. Then the mixture was diluted with EtOAc, washed with NaCl-solution and dried over Na2 SO4. Evaporation gave a brown oil. The crude product was purified by chromatography (silica gel, methanol/EtOAc) to yield a white solid.

Workup

  1. washwashed with NaCl-solution
  2. customdried over Na2 SO4
  3. customEvaporation
  4. customgave a brown oil
  5. customThe crude product was purified by chromatography (silica gel, methanol/EtOAc)
  6. customto yield a white solid

Sources & evidence

ORD record
ord-7a9ec2e691b2477da11df1940e2ef5aa
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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