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

HRID 10994

Reaction equation

C(OC(=O)NC(=N)C1C=CC(CNC([C@H]2N3C(=O)C(NS(C)(=O)=O)=CN=C3CC2)=O)=CC=1)(C)(C)C.C(OC(=O)NC(C1C=CC(CNC([C@H]2N3C(=O)C(N(CC)CC)=CN=C3CC2)=O)=CC=1)=N)(C)(C)C.C(OC(=O)NC(=N)C1C=CC(CNC([C@H]2N3C(=O)C([NH:98][S:99]([C:102]4[C:111]5[C:106](=[CH:107][CH:108]=[CH:109][CH:110]=5)[CH:105]=[CH:104][CH:103]=4)(=[O:101])=[O:100])=CN=C3CC2)=O)=CC=1)(C)(C)C>>[C:102]1([S:99]([NH2:98])(=[O:100])=[O:101])[C:111]2[C:106](=[CH:107][CH:108]=[CH:109][CH:110]=2)[CH:105]=[CH:104][CH:103]=1

Participants

Reactant 3

HCID 145857221tert-butyl N-[4-[[[(6S)-3-(naphthalen-1-ylsulfonylamino)-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

HCID 145857232tert-butyl N-[4-[[[(6S)-3-(methanesulfonamido)-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

HCID 145857233tert-butyl N-[4-[[[(6S)-3-(diethylamino)-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

Product 1

HCID 163571NaphthalenesulfonamideYield 30%

Procedure

Following a procedure similar to that for the preparation of 16a, intermediate 3a (50 mg, 0.117 mmol) and 1-napthylene sulfonyl chloride (39.8 mg, 0.176 mmol) yielded 21.7 mg (30.0%) of 1-napthalene sulfonamide intermediate 30a. MS (ESI) 617.0 (M+H+).

Sources & evidence

ORD record: ord-52e7df54d8284410b978de744febdd8b
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094783B2

Linked notes

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