HCID 58305759, compound → HCID 58305745, compound

HRID 2280315Notes

Reaction equation

HRID 2280315 reaction equation
[CH2:1]([C:3](Cl)=[O:4])[CH3:2].C(Cl)Cl.[N:9]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:24]([C:25]4[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][C:26]=4[CH3:32])[C:23]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH:13]=[CH:12][N:11]=[CH:10]1>N1C=CC=CC=1>[N:9]1([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[N:24]([C:25]4[CH:30]=[CH:29][C:28]([NH:31][C:3](=[O:4])[CH2:1][CH3:2])=[CH:27][C:26]=4[CH3:32])[C:23]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 58305759HCID 58305759, compoundHCID 131733500HCID 131733500, compound

Product 1

HCID 58305745HCID 58305745, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of pyridine (1 mL) and C2H5COCl/DCM (v/v=1/100, 4.2 mL) was added a solution of 20B (see scheme 20) (150 mg, 0.389 mmol) in pyridine (1 mL) at 0° C. The mixture was stirred at room temperature overnight. The solvents were removed under reduced pressure and the resulting solid was acidified with 10% hydrochloric acid to pH=5.0. The resulting precipitate was isolated by centrifuge, rinsed with water, dried under reduced pressure to afford the crude product as a brown powder, After purification by prep-HPLC, 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(2-methyl-4-propionamidophenyl)-1H-pyrrol-2-yl)propanoic acid (32 mg, 19%) was obtained as a brown oil.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customThe resulting precipitate was isolated by centrifuge
  3. washrinsed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-5119188d767743df8b71a3e280853a5f
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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