1,1'-Carbonyldiimidazole → HCID 59471686, compound

HRID 78558

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[NH2:12][C:13]1[N:14]=[CH:15][C:16]([C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)C(O)=O)=[N:17][C:18]=1[C:19](=[O:27])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1N=CN([C:42](N2C=NC=C2)=[O:43])C=1.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.CS(C)=O>[NH2:12][C:13]1[C:18]([C:19]([NH:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:27])=[N:17][C:16]([C:28]2[CH:36]=[CH:35][C:34]([C:42]([N:1]3[CH2:5][CH2:4][CH2:3][C@@H:2]3[CH2:6][N:7]3[CH2:11][CH2:10][CH2:9][CH2:8]3)=[O:43])=[CH:30][CH:29]=2)=[CH:15][N:14]=1

Participants

Conditions

Temperature: 38 °C

Procedure

1-[[(2R)-pyrrolidin-2-yl]methyl]pyrrolidine (69.23 mg, 0.449 mmol) was weighed into a greenhouse tube and treated with a solution of 3-(5-amino-6-(phenylcarbamoyl)pyrazin-2-yl)benzoic acid (50 mg, 0.150 mmol), CDI (48.51 mg, 0.299 mmol) and DMAP (1.82 mg, 0.015 mmol) in DMSO (1 mL of a stock solution). DIPEA (78.2 uL, 0.449 mmol) was then added and the mixture stirred at 38° C. for 6 hours. The reaction mixture was filtered and the resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100 A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were freeze-dried to give the title compound as a solid (51.87 mg, 73% Yield).

Workup

filtrationThe reaction mixture was filtered
customthe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100 A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
customThe fractions were freeze-dried

Sources & evidence

ORD record: ord-e41d59218ed049c59525f2f1bd958d5d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841308B2

Linked notes

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