Triethylamine → HCID 118341222, compound

HRID 1753002Notes

Reaction equation

HRID 1753002 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[N:12]([CH:19]([CH3:21])[CH3:20])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1.[CH:22]1([C:25]2[O:26][C:27]([CH3:34])=[C:28]([CH2:30][C:31](O)=[O:32])[N:29]=2)[CH2:24][CH2:23]1.C(N(CC)CC)C.CCCP(=O)=O>C1COCC1>[CH:22]1([C:25]2[O:26][C:27]([CH3:34])=[C:28]([CH2:30][C:31]([NH:1][C:2]3[CH:7]=[N:6][CH:5]=[C:4]([C:8]([C:10]4[C:14]5[CH:15]=[N:16][CH:17]=[CH:18][C:13]=5[N:12]([CH:19]([CH3:21])[CH3:20])[CH:11]=4)=[O:9])[CH:3]=3)=[O:32])[N:29]=2)[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 16167369Propylphosphoric anhydrideHCID 24254169HCID 24254169, compoundHCID 90093167HCID 90093167, compound

Product 1

HCID 118341222HCID 118341222, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (5-aminopyridin-3-yl)(1-isopropyl-1H-pyrrolo[3,2-c]pyridin-3-yl)methanone (Preparation 19, 80 mg, 0.285 mmol) and (2-cyclopropyl-5-methyl-1,3-oxazol-4-yl)acetic acid (Preparation 87, 52 mg, 0.285 mmol) in THF (5 mL) was added triethylamine (138 uL, 0.997 mmol) and propylphosphonic anhydride (429 uL, 0.712 mmol). The reaction was stirred at room temperature for 18 hours. The reaction was concentrated to dryness and purified using preparative HPLC to afford the title compound as a white solid (50 mg, 39%).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. custompurified

Sources & evidence

ORD record
ord-da0e0bfdc3314343822d512c611f9a1e
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

Loading…