Dimethylformamide → HCID 66662432, compound

HRID 557870Notes

Reaction equation

HRID 557870 reaction equation
CN1CCOCC1.[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2([C:21]([OH:23])=O)[CH2:20][CH2:19]2)=[CH:10][CH:9]=1.Cl.Cl.[F:26][C:27]1[C:32]2[C:33](=[O:40])[O:34][C:35]3([CH2:39][CH2:38][NH:37][CH2:36]3)[C:31]=2[CH:30]=[CH:29][N:28]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.CN(C)C=O>>[F:26][C:27]1[C:32]2[C:33](=[O:40])[O:34][C:35]3([CH2:39][CH2:38][N:37]([C:21]([C:18]4([C:11]5[C:12]6[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=6)[N:8]=[CH:9][CH:10]=5)[CH2:19][CH2:20]4)=[O:23])[CH2:36]3)[C:31]=2[CH:30]=[CH:29][N:28]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 2724699PyBOPHCID 66662046HCID 66662046, compoundHCID 66662416HCID 66662416, compound

Product 1

HCID 66662432HCID 66662432, compound

Procedure

HCl in dioxane (4.0 M, 1 mL) was added to tert-butyl 4-fluoro-3-oxo-1′H,3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidine]-1′-carboxylate (25.8 mg, 0.0000837 mol). The reaction mixture was stirred at room temperature for 30 minutes before the volatiles was removed to afford the free amine (hydrochloric acid salt), which was subsequently used in the coupling reaction. 4-Methylmorpholine (50 μL, 0.0004 mol) was added to a mixture of 1-quinolin-4-ylcyclopropanecarboxylic acid (17.8 mg, 0.0000837 mol), 4-fluoro-3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one dihydrochloride (23.5 mg, 0.0000837 mol), and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (45.7 mg, 0.0000879 mol) in N,N-dimethylformamide (0.5 mL, 0.006 mol). The reaction mixture was stirred at room temperature for 2 hours. The crude product was purified by prep-LCMS. LC/MS: 402.1 (M+H+).

Workup

  1. customwas subsequently used in the coupling reaction
  2. customThe crude product was purified by prep-LCMS

Sources & evidence

ORD record
ord-63e2d2b9f66146dda51f1ca36ad34065
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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