Cyclopropylamine → (S)-tert-Butyl 1-(2-(cyclopropylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamate

HRID 525038Notes

Reaction equation

HRID 525038 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:22])[C:10]([NH:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]([O:20]C)=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]1([NH2:26])[CH2:25][CH2:24]1>>[CH:23]1([NH:26][C:18]([C:14]2[N:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:22])[CH:17]=[CH:16][CH:15]=2)=[O:20])[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 86722033(S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate

Product 1

HCID 86722057(S)-tert-Butyl 1-(2-(cyclopropylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamate

Procedure

Same procedure as described in preparation 133a was used from (S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate (900 mg, 80% purity, 2.28 mmols) and cyclopropanamine (0.48 ml, 6.86 mmols). After 3.5 h stirring at 80° C. the title compound was obtained (589 mg, 77%).

Sources & evidence

ORD record
ord-715fbf15e75e4de5a76ef1b96342dbf6
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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