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Triethylamine → 9-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-3,3-dimethylnonanal

HRID 1689540
Notes
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Reaction equation

HRID 1689540 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([N:11]2[CH2:16][C:15]3([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[O:14][CH2:13][CH2:12]2)=[O:10])[N:8]=1)([CH3:3])[CH3:2].FC(F)(F)C([O-])=O.C(N(CC)CC)C.CS(O[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([CH3:52])([CH3:51])[CH2:48][CH:49]=[O:50])(=O)=O>C(#N)C>[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([N:11]2[CH2:16][C:15]3([CH2:17][CH2:18][N:19]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([CH3:51])([CH3:52])[CH2:48][CH:49]=[O:50])[CH2:20][CH2:21]3)[O:14][CH2:13][CH2:12]2)=[O:10])[N:8]=1)([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 84468TrifluoroacetateHCID 579889227,7-Dimethyl-9-oxononyl methanesulfonateHCID 57989152(2-Isopropylthiazol-4-yl)-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Product 1

HCID 579893649-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-3,3-dimethylnonanal

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent2×

Procedure

(2-Isopropyl-thiazol-4-yl)-(1-oxa-4,9-diaza-spiro[5.5]undec-4-yl)-methanone (0.262 g) (prepared from the trifluoroacetate salt as in Example 102, step c) was dissolved in acetonitrile (4 mL) and triethylamine (0.22 mL) was added. This solution was then added to a solution of 7,7-dimethyl-9-oxononyl methanesulfonate (Example 279, step e) (0.291 g) in acetonitrile (4 mL) and the resultant mixture heated at 80° C. overnight. The solvents were removed under vacuum. Purification was by silica gel chromatography eluting with 0-10% Methanol in DCM to afford the subtitled compound as a colourless oil. Yield 0.361 g.

Workup

  1. customThe solvents were removed under vacuum
  2. customPurification
  3. washeluting with 0-10% Methanol in DCM

Sources & evidence

ORD record
ord-f8d5bfd3855344a99c2f7df2004965c1
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148373B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes