3-benzyloxycarbonylamino-6-ethyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid → benzyl N-[6-ethyl-6-[[4-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]phenyl]methylcarbamoyl]-4-oxo-7,8-dihydropyrrolo[1,2-a]pyrimidin-3-yl]carbamate

HRID 10982Notes

Reaction equation

HRID 10982 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]2[C:19]([CH2:25][CH3:26])([C:22]([OH:24])=O)[CH2:20][CH2:21][C:15]2=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:31][C:32](=[O:44])[NH:33][C:34]([C:36]1[CH:41]=[CH:40][C:39]([CH2:42][NH2:43])=[CH:38][CH:37]=1)=[NH:35])([CH3:30])([CH3:29])[CH3:28]>>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C:12]1[C:17](=[O:18])[N:16]2[C:19]([C:22](=[O:24])[NH:43][CH2:42][C:39]3[CH:40]=[CH:41][C:36]([C:34]([NH:33][C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:44])=[NH:35])=[CH:37][CH:38]=3)([CH2:25][CH3:26])[CH2:20][CH2:21][C:15]2=[N:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 219796213-benzyloxycarbonylamino-6-ethyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic AcidHCID 145832046tert-butyl N-[4-(aminomethyl)benzenecarboximidoyl]carbamate

Product 1

HCID 145857217benzyl N-[6-ethyl-6-[[4-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]phenyl]methylcarbamoyl]-4-oxo-7,8-dihydropyrrolo[1,2-a]pyrimidin-3-yl]carbamateYield 100%

Procedure

According to the procedure for the preparation of intermediate 19c, intermediate 22b (34.5 mg, 0.0965 mmol) was coupled with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid tert-butyl ester to afford 57 mg (100%) of intermediate 22c.

Sources & evidence

ORD record
ord-fb6ccc65119b4e95b56e88ab95c1b6e5
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Reaction notes

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