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Cyclopentanone → tert-butyl N-[4-[[[(6S)-3-(cyclopentylamino)-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

HRID 10961
Notes
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Reaction equation

HRID 10961 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([C@H:20]2[N:24]3[C:25](=[O:37])[C:26]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=CC=4)=[CH:27][N:28]=[C:23]3[CH2:22][CH2:21]2)=[O:19])=[CH:12][CH:11]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)NC(C1C=CC(CNC([C@H]2N3C(=O)C(N)=CN=C3CC2)=O)=CC=1)=N)(C)(C)C.C1(=O)CCCC1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([C@H:20]2[N:24]3[C:25](=[O:37])[C:26]([NH:29][CH:30]4[CH2:31][CH2:36][CH2:35][CH2:34]4)=[CH:27][N:28]=[C:23]3[CH2:22][CH2:21]2)=[O:19])=[CH:12][CH:11]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 8452CyclopentanoneHCID 5049666Sodium triacetoxyborohydrideHCID 145857226tert-butyl N-[4-[[[(6S)-3-amino-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamateHCID 145857234tert-butyl N-[4-[[[(6S)-3-(benzylamino)-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

Product 1

HCID 145857225
tert-butyl N-[4-[[[(6S)-3-(cyclopentylamino)-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate
Yield 57.3%

Procedure

Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (115.2 mg, 0.27 mmol), cyclopentanone (68.1 mg, 0.81 mmol) and NaBH(OAc)3 (217.5 mg, 1.03 mmol) yielded 76.5 mg (57.3%) of intermediate 6a. MS (ESI) 496.1 (M+H+).

Sources & evidence

ORD record
ord-77ff826270494a869c96dd5332baae40
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094783B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes