Diisopropylethylamine → HCID 68000648, compound

HRID 336530Notes

Reaction equation

FC(F)(F)C(O)=O.[CH2:8]1[C:11]2([CH2:15][CH2:14][NH:13][CH2:12]2)[CH2:10][CH:9]1[NH:16][C:17]([O:19][CH2:20][C:21]1[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:22]=1)=[O:18].F[C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[CH:34][N:33]=1.C(N(CC)C(C)C)(C)C>>[F:44][C:41]1[CH:40]=[CH:39][C:38]([C:35]2[CH:36]=[CH:37][C:32]([N:13]3[CH2:14][CH2:15][C:11]4([CH2:10][CH:9]([NH:16][C:17]([O:19][CH2:20][C:21]5[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:22]=5)=[O:18])[CH2:8]4)[CH2:12]3)=[N:33][CH:34]=2)=[CH:43][CH:42]=1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 46312742HCID 46312742, compound

HCID 68001495HCID 68001495, compound

Product 1

HCID 68000648HCID 68000648, compoundYield 19.4%

Procedure

The process is performed according to the procedure described in Example 1 (step 1.3.). Starting with 0.45 g (1.04 mmol) of ethyl 5-(6-azaspiro[3.4]oct-2-ylcarbamoyloxymethyl)isoxazole-3-carboxylate trifluoroacetate, described in step 6.6., 0.198 g (1.04 mmol) of 2-fluoro-5-(4-fluorophenyl)pyridine, prepared in step 6.7. and 0.40 g (3.12 mmol) of N,N-diisopropylethylamine, and after purification by chromatography on preparative plates, eluting with a 96/4 mixture of dichloromethane and methanol, 0.10 g of pure product is obtained in the form of a wax, which is used without further purification in the following step.

Workup

washeluting with a 96/4 mixture of dichloromethane and methanol

Sources & evidence

ORD record: ord-252fbef23ca64fffb24a5ff214b6921a
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889702B2

Reaction notes

Loading…