3-Aminoazetidine, 3-BOC protected → HCID 60208257, compound

HRID 2221024Notes

Reaction equation

HRID 2221024 reaction equation
CC([N:5]([CH:9]1[CH2:12][N:11](/[C:13](/[NH:25][C:26]2[CH:35]=[C:34]3[C:29]([C:30](=[O:45])[N:31]([CH2:36][CH2:37][C:38]4[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=4)[CH:32]=[N:33]3)=[CH:28][CH:27]=2)=[N:14]\[C@H:15]2[CH2:20][C@H:19]3[CH2:21][C@H:17]([C:18]3([CH3:23])[CH3:22])[C@@H:16]2[CH3:24])[CH2:10]1)C(=O)[O-])(C)C.N1CC(NC(=O)OC(C)(C)C)C1.Cl.O1CCOCC1>>[NH2:5][CH:9]1[CH2:10][N:11]([C:13](=[N:14][C@H:15]2[CH2:20][C@H:19]3[CH2:21][C@H:17]([C:18]3([CH3:23])[CH3:22])[C@@H:16]2[CH3:24])[NH:25][C:26]2[CH:35]=[C:34]3[C:29]([C:30](=[O:45])[N:31]([CH2:36][CH2:37][C:38]4[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=4)[CH:32]=[N:33]3)=[CH:28][CH:27]=2)[CH2:12]1

Participants

4

Reactant 3

HCID 15194053-Aminoazetidine, 3-BOC protectedHCID 204431481,4-Dioxane hydrochlorideHCID 178461489HCID 178461489, compound

Product 1

HCID 60208257HCID 60208257, compound

Procedure

1,1-dimethylethyl[1-((Z)-({3-[2-(4-fluorophenyl)ethyl]-4-oxo-3,4-dihydro-7-quinazolinyl}amino){[(1S,2S,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]imino}methyl)-3-azetidinyl]carbamate (synthesized using 1,1-dimethylethyl 3-azetidinylcarbamate by the methods described previously) was treated with 4.0 N HCl/dioxane (4 mL) and stirred overnight. The reaction was then purified by preparatory HPLC to provide 3-amino-N-{3-[2-(4-fluorophenyl)ethyl]-4-oxo-3,4-dihydro-7-quinazolinyl}-N′-[(1S,2S,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]-1-azetidinecarboximidamide as a white solid. LC/MS: M+H 517.20 at 2.19 minutes, Method D.

Workup

  1. customThe reaction was then purified by preparatory HPLC

Sources & evidence

ORD record
ord-ce5659f5331646ec964b6c6857ed82d8
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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