Dimethylformamide → HCID 178488306, compound

HRID 1753124Notes

Reaction equation

[N-]=[N+]=[N-].[Na+].[Cl-].[NH4+:6].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]23[NH:32][CH2:31][CH2:30][N:16]2[C:17](=[O:29])[C:18]2[N:19]([CH:21]=[C:22]([C:24]4[NH:28][N:27]=[N:26][N:25]=4)[CH:23]=2)[CH2:20]3)=[CH:11][CH:10]=1.CN([CH:36]=[O:37])C>>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]23[N:32]([C:9]([C:10]4[C:11]([CH3:12])=[N:6][O:37][CH:36]=4)=[O:8])[CH2:31][CH2:30][N:16]2[C:17](=[O:29])[C:18]2[N:19]([CH:21]=[C:22]([C:24]4[NH:28][N:27]=[N:26][N:25]=4)[CH:23]=2)[CH2:20]3)=[CH:11][CH:10]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 25517Ammonium Chloride

HCID 33557Sodium Azide

HCID 178488305HCID 178488305, compound

Product 1

HCID 178488306HCID 178488306, compoundYield 13%

Conditions

Temperature: 120 °C

Procedure

Sodium azide (33 mg, 0.51 mmol) and ammonium chloride (27 mg, 0.51 mmol) was added to a solution of 10a-(4-methoxyphenyl)-7-(1H-tetrazol-5-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (150 mg, 0.43 mmol) in DMF and heated in a sealed tube at 120° C. for 16 hours. The reaction mixture was concentrated and purified by flash chromatography to give 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-(1H-tetrazol-5-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (75) as a white solid (28 mg, yield 13%). Compounds 145 and 146 were similarly prepared using General Method A: Route (c) as follows.

Workup

concentrationThe reaction mixture was concentrated
custompurified by flash chromatography

Sources & evidence

ORD record: ord-a64352f1454a4b16b2dc4ca5f006f844
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163029B2

Reaction notes

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