Glycolic Acid → HCID 89613091, compound

HRID 1403170Notes

Reaction equation

HRID 1403170 reaction equation
[F:1][CH:2]([F:31])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([O:20][C@@H:21]3[CH2:25][CH2:24][C@@H:23]([NH2:26])[CH2:22]3)[CH:9]=2)[C:6]2[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=2[N:4]=1.[C:32](O)(=[O:35])[CH2:33][OH:34].ON1C2C=CC=CC=2N=N1.N=C=N.[N-]=C=O.C(=O)([O-])[O-]>CN(C)C=O>[F:31][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=[C:10]([O:20][C@@H:21]3[CH2:25][CH2:24][C@@H:23]([NH:26][C:33](=[O:34])[CH2:32][OH:35])[CH2:22]3)[CH:9]=2)[C:6]2[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=2[N:4]=1

Participants

8

Reactant 6

HCID 757Glycolic AcidHCID 19660Carbonate IonHCID 757711-HydroxybenzotriazoleHCID 105034IsocyanateHCID 160435CarbodiimideHCID 89612991HCID 89612991, compound

Product 1

HCID 89613091HCID 89613091, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of rel-(1R,3R)-3-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclopentanamine (10.8 mg), glycolic acid (1.9 mg), and 1-hydroxybenzotriazole (3.4 mg) in N,N-dimethylformamide (1.0 mL) was added a PS-Carbodiimide (Biotage Inc.) (100 mg), followed by stirring at room temperature overnight. To the reaction solution were added a PS-Isocyanate (Biotage Inc.) (50 mg) and a MP-Carbonate (Biotage Inc.) (50 mg), followed by stirring for four hours, and the insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure to obtain rel-N-[(1R,3R)-3-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclopentyl]-2-hydroxyacetamide (7.2 mg).

Workup

  1. stirringby stirring for four hours
  2. customthe insoluble matter was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49165c883a904880b0250806b60e992b
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

Loading…