2-Aminothiazole → 1-Benzyl-1H-pyrrole-2-carboxylic acid

HRID 1159162Notes

Reaction equation

HRID 1159162 reaction equation
N1C=CC=C1C(OCC)=O.C(Br)C1C=CC=CC=1.[CH2:19]([N:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31]([OH:33])=[O:32])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH2:34][C:35]1[S:36][CH:37]=[CH:38][N:39]=1>>[CH2:19]([N:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31]([OH:33])=[O:32])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1.[S:36]1[CH:37]=[CH:38][N:39]=[C:35]1[NH:34][C:31]([C:27]1[N:26]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:30]=[CH:29][CH:28]=1)=[O:33]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 7498Benzyl BromideHCID 255670Ethyl 1H-pyrrole-2-carboxylateHCID 149858391-Benzyl-1H-pyrrole-2-carboxylic acid

Product 2

HCID 149858391-Benzyl-1H-pyrrole-2-carboxylic acidHCID 59513988HCID 59513988, compound

Procedure

1-Benzyl-pyrrole-2-carboxylic acid (1.12 g) was prepared from ethyl pyrrole-2-carboxylate (1.39 g, 10.0 mmol) and benzyl bromide (1.26 mL, 11.0 mmol) following general procedures A and B. 1-Benzyl-pyrrole-2-carboxylic acid thiazol-2-ylamide (45 mg) was prepared from 1-benzyl-pyrrole-2-carboxylic acid (50 mg, 0.25 mmol) and 2-aminothiazole (25 mg, 0.25 mmol) following the general procedure F.

Sources & evidence

ORD record
ord-d32969782fc5418b8d40c5c33819e9c3
Source dataset
uspto-grants-2010_10
Patent number
US07812043B2

Reaction notes

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