1,1'-Carbonyldiimidazole → HCID 86305424, compound

HRID 712714Notes

Reaction equation

HRID 712714 reaction equation
[C:1]([N:4]1[C:13]2[N:12]=[CH:11][C:10]([C:14]3[CH:15]=[C:16]([CH2:20][C:21](O)=[O:22])[CH:17]=[N:18][CH:19]=3)=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1)(=[O:3])[NH2:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[F:37][C:38]1([F:44])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[F:37][C:38]1([F:44])[CH2:43][CH2:42][N:41]([C:21](=[O:22])[CH2:20][C:16]2[CH:15]=[C:14]([C:10]3[CH:9]=[C:8]4[C:13](=[N:12][CH:11]=3)[N:4]([C:1]([NH2:2])=[O:3])[CH2:5][CH2:6][CH2:7]4)[CH:19]=[N:18][CH:17]=2)[CH2:40][CH2:39]1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 86305421HCID 86305421, compound

Product 1

HCID 86305424HCID 86305424, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of [5-(8-carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-yl]-acetic acid (25 mg, 0.080 mmol) in DMF (1.5 mL) is added 1,1′-carbonyldiimidazole (14 mg, 0.088 mmol) and the mixture is stirred at room temperature for 16 h. 4,4-Difluoro-piperidine hydrochloride salt (15 mg, 0.096 mmol) and N,N-diisopropylethylamine (0.042 mL, 0.24 mmol) are added and stifling continues for an additional 16 h. H2O is added and the resulting precipitate is collected by filtration to afford 21 mg of the titled product.

Workup

  1. waitstifling continues for an additional 16 h
  2. filtrationthe resulting precipitate is collected by filtration

Sources & evidence

ORD record
ord-e1105bf5fc854f9db757854be4bb08ab
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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