Diisopropylethylamine → 3-(Benzyloxy)-N-(4-fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzyl)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxamide

HRID 1093121Notes

Reaction equation

HRID 1093121 reaction equation
[CH2:1]([O:8][C:9]1[C:21](=[O:22])[N:13]2[CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([C:12]2=[N:11][C:10]=1[C:23]([OH:25])=O)[CH2:17][CH2:16]3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[F:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[C:30]([N:36]2[CH2:40][C:39]([CH3:42])([CH3:41])[N:38]([CH3:43])[S:37]2(=[O:45])=[O:44])[CH:29]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C1C=CN=CC=1.CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:21](=[O:22])[N:13]2[CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([C:12]2=[N:11][C:10]=1[C:23]([NH:35][CH2:34][C:31]1[CH:32]=[CH:33][C:28]([F:27])=[CH:29][C:30]=1[N:36]1[CH2:40][C:39]([CH3:41])([CH3:42])[N:38]([CH3:43])[S:37]1(=[O:45])=[O:44])=[O:25])[CH2:17][CH2:16]3)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579050733-(Benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylic acidHCID 665889041-(4-Fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)phenyl)methanamine hydrochloride salt

Product 1

HCID 579052343-(Benzyloxy)-N-(4-fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzyl)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylic acid (0.03 g, 0.088 mmol), 1-(4-fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)phenyl)methanamine hydrochloride salt (0.043 g, 0.132 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (0.100 g, 0.264 mmol), 4-(dimethylamino)pyridine (DMAP) (1.074 mg, 8.79 μmol) and diisopropyl ethylamine (0.077 mL, 0.439 mmol) in DMF (2 mL) was stirred at room temperature for 1 h. The mixture was diluted with ethyl acetate and washed with 0.5 N HCl, water followed by brine. The organic phase was dried (Na2SO4), filtered and concentrated to give the title compound as a crude yellow oil. LCMS (M+H) calcd for C30H36FN6O5S: 611.24; found: 611.33.

Workup

  1. washwashed with 0.5 N HCl, water
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6aef91fa95c34226b6ccd8e1c01cb440
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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