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Diisopropylethylamine → Tert-butyl 4-(3-bromoimidazo[1,2-b]pyridazin-6-yl)-1,4-diazepane-1-carboxylate

HRID 870744
Notes
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Reaction equation

HRID 870744 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[C:8](F)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[N:12]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>CC(O)C>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([N:15]3[CH2:16][CH2:17][CH2:18][N:12]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][CH2:14]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 866963183-Bromo-6-fluoroimidazo[1,2-b]pyridazine

Product 1

HCID 68647817Tert-butyl 4-(3-bromoimidazo[1,2-b]pyridazin-6-yl)-1,4-diazepane-1-carboxylateYield 195.9%

Reagents, catalysts & solvents 1

HCID 3776Isopropanol
Solvent

Procedure

A stirred solution of 3-bromo-6-fluoroimidazo[1,2-b]pyridazine (1.6 g, 7.6 mmol), tert-butyl 1,4-diazepane-1-carboxylate [112275-50-0] (4.4 mL, 22.6 mmol), and Hunig's base [7087-68-5] (5.3 mL, 30.4 mmol) in 2-propanol (25 mL) was heated to 65° C. for 3d then partitioned between brine and ethyl acetate. The extract was dried (CaSO4) and evaporated to provide 5.9 g of clear orange liquid which was flash chromatographed (silica gel eluted with 10% (v/v) methanol/ethyl acetate) and crystallized from ethyl acetate/heptane to afford 2.0 g of white powder, mp. 101-102° C. 1H NMR (400 MHz, DMSO-d6) δ ppm (rotomers present) 1.03 (s, 5H) 1.17 (s, 4H) 1.73 (br. s., 1H) 1.85 (br. s., 1H) 2.43-2.47 (m, 1H) 3.20-3.29 (m, 3H) 3.49 (d, J=5.51 Hz, 1H) 3.55-3.66 (m, 3H) 3.70-3.79 (m, 2H) 7.05 (d, J=9.92 Hz, 1H) 7.49 (d, J=7.28 Hz, 1H) 7.78 (d, J=9.70 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ ppm (rotomers present) 24.50, 24.83, 27.45, 27.61, 44.10, 44.78, 44.83, 45.33, 47.58, 47.74, 48.01, 48.09, 78.11, 78.27, 98.80, 109.23, 109.61, 125.65, 125.77, 130.81, 130.89, 136.07, 153.01, 153.18, 153.90, 154.19. LRMS (ESI) m/z 396.1/398.1 [(M+H)]+, calc'd for C16H22BrN5O2: 396.29.

Workup

  1. customthen partitioned between brine and ethyl acetate
  2. dry with materialThe extract was dried (CaSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-7aea33d7937c45548a4ae31e6634f7ce
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08969565B2

Reaction notes

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