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Diisopropylethylamine → HCID 57904985, compound

HRID 1093126
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Reaction equation

HRID 1093126 reaction equation
[NH2:1][C:2]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[CH2:5][N:4]1[C:11](=[O:27])[C:12]([OH:26])=[C:13]([C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[O:16])[N:14]=[C:3]21.[F:28][CH2:29][CH2:30][N:31]([CH3:37])[C:32](=[O:36])[C:33](O)=[O:34].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.CN(C=O)C.Cl>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][NH:17][C:15]([C:13]2[N:14]=[C:3]3[C:2]4([NH:1][C:33](=[O:34])[C:32]([N:31]([CH2:30][CH2:29][F:28])[CH3:37])=[O:36])[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10]4)[CH2:5][N:4]3[C:11](=[O:27])[C:12]=2[OH:26])=[O:16])=[CH:24][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 55301814N-(2-fluoroethyl)-N-methyloxamic acidHCID 5790475010-Amino-N-(4-fluorobenzyl)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide

Product 1

HCID 57904985
HCID 57904985, compound
Yield 64.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 10-amino-N-(4-fluorobenzyl)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide (0.05 g, 0.122 mmol), 2-((2-fluoroethyl)(methyl)amino)-2-oxoacetic acid (0.036 g, 0.245 mmol), diisopropyl ethylamine (0.128 mL, 0.734 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (0.093 g, 0.245 mmol) and 4-(dimethylamino)pyridine (DMAP) (2.99 mg, 0.024 mmol) in DMF (1.2 mL) was stirred at room temperature for 16 h. The mixture was diluted with 1N HCl and extracted with ethyl acetate. Solids precipitated out of the biphasic mixture and were collected by filtration to give the title compound as white needles (0.0394 g, 60% yield). 1H NMR (500 MHz, CDCl3) δ: 11.92-12.05 (1 H, m), 8.16-8.68 (2 H, m), 7.28-7.42 (2 H, m), 6.91-7.10 (2 H, m), 4.37-4.75 (4 H, m), 4.16 (2 H, t, J=4.58 Hz), 3.94-4.08 (1 H, m), 3.50-3.65 (1 H, m), 2.91-3.43 (3 H, m), 2.53-2.66 (2 H, m), 2.45-2.52 (1 H, m), 1.88-2.11 (4 H, m), 1.61-1.78 (2 H, m). LCMS (M+H) calcd for C24H28F2N5O5: 504.20; found: 504.02.

Workup

  1. extractionextracted with ethyl acetate
  2. customSolids precipitated out of the biphasic mixture
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4bcc2083f7694133a1c2cf8a797f6dac
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129398B2

Reaction notes

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