Triethylamine → HCID 178475048, compound

HRID 1441382Notes

Reaction equation

HRID 1441382 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][C@@H:11]([NH:14][C:15](=[O:17])[CH3:16])[CH2:10]2)=[CH:5][CH:4]=1.[C:18]([O:22][C:23](=[O:39])[NH:24]/[C:25](/N1C=CC=N1)=[N:26]/[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>C(Cl)Cl>[C:29]([O:28][C:27](=[O:33])[NH:26]/[C:25](/[NH:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:13][CH2:12][C@@H:11]([NH:14][C:15](=[O:17])[CH3:16])[CH2:10]2)=[CH:7][CH:8]=1)=[N:24]/[C:23](=[O:39])[O:22][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6383521N,N'-Di-Boc-1H-pyrazole-1-carboximidamideHCID 131727868N-[(3R)-1-(4-aminophenyl)pyrrolidin-3-yl]acetamide mono hydrochloride

Product 1

HCID 178475048HCID 178475048, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(3R)-1-(4-aminophenyl)pyrrolidin-3-yl]acetamide mono hydrochloride (Method 44, 3.31 g, 15 mmol), di-tert-butyl[(Z)-1H-pyrazol-1-ylmethylylidene]biscarbamate (5.91 g, 15 mmol) and triethylamine (4.17 ml, 30 mmol) in DCM (50 ml) were heated at 40° C. for 18 hours. After evaporation under reduced pressure, chromatography on silica gel with ethyl acetate/isohexane (50:50 to 100) gave di-tert-butyl[(E)-({4-[(3R)-3-(acetylamino)pyrrolidin-1-yl]phenyl}amino)methylylidene]biscarbamate, which was dissolved in DCM (80 ml) and treated with TFA (15 ml) at ambient temperature for 18 hours under nitrogen. After evaporation under reduced pressure, the residue was dissolved in MeOH (20 ml) and diluted with ether. The title compound was collected by filtration as an off white solid (1.79 g, 30% over two steps). NMR: 1.80 (s, 3H), 1.81-1.93 (m, 1H), 2.10-2.27 (m, 1H), 2.99-3.06 (m, 1H), 3.19-3.51 (m, 3H), 4.27-4.39 (m, 1H), 6.52 (d, 2H), 7.03 (d, 2H), 7.16 (s, 3H), 8.10 (d, 1H), 9.36 (s, 1H).

Workup

  1. customAfter evaporation under reduced pressure, chromatography on silica gel with ethyl acetate/isohexane (50:50 to 100)

Sources & evidence

ORD record
ord-e4a78fca4c9845e5aedb86e2aa18e6d2
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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