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

HRID 1864518Notes

Reaction equation

HRID 1864518 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][C:15]([NH:21]/[C:22](=[N:35]/[C@H:36]4[CH2:41][C@H:40]5[CH2:42][C@H:38]([C:39]5([CH3:44])[CH3:43])[C@@H:37]4[CH3:45])/[N:23]4[CH2:26][CH:25]([NH:27]C(=O)OC(C)(C)C)[CH2:24]4)=[CH:16][CH:17]=3)[N:12]=[CH:11]2)=[CH:4][CH:3]=1.N1CC(NC(=O)OC(C)(C)C)C1.Cl.O1CCOCC1>>[NH2:27][CH:25]1[CH2:24][N:23]([C:22](=[N:35][C@H:36]2[CH2:41][C@H:40]3[CH2:42][C@H:38]([C:39]3([CH3:44])[CH3:43])[C@@H:37]2[CH3:45])[NH:21][C:15]2[CH:14]=[C:13]3[C:18]([C:19](=[O:20])[N:10]([CH2:9][CH2:8][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH:11]=[N:12]3)=[CH:17][CH:16]=2)[CH2:26]1

Participants

4

Reactant 3

HCID 15194053-Aminoazetidine, 3-BOC protectedHCID 204431481,4-Dioxane hydrochlorideHCID 178461490HCID 178461490, 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-13467d4616fa4591b9505e4f718250a8
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

Loading…