Acetone → Acetoacetic Acid

HRID 2390654Notes

Reaction equation

HRID 2390654 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:24])[O:19]C(C)(C)C)=[C:13]([O:25][CH3:26])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:27]=[CH:28]/[CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[CH:4][N:3]=1.[CH3:35][C:36]([CH3:38])=[O:37]>Cl>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5](/[CH:27]=[CH:28]/[CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[C:6]=3[S:10][CH:9]=2)=[CH:12][C:13]=1[O:25][CH3:26].[CH3:35][C:36]([CH2:38][C:18]([OH:24])=[O:19])=[O:37]

Participants

5

Reactant 2

HCID 180AcetoneHCID 18451456Tert-butyl 4-{4-amino-7-[(1e)-3-(diethylamino)-1-propenyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenylcarbamate

Product 2

HCID 96Acetoacetic AcidHCID 184507083-(4-Amino-3-methoxyphenyl)-7-[(1e)-3-(diethylamino)-1-propenyl]thieno[3,2-c]pyridin-4-amine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of Example 365B (425 mg, 0.88 mmol) in acetone (10 mL) and 6N aqueous hydrochloric acid (2 mL) was stirred for 18 hours at ambient temperature then concentrated under reduced pressure. The residue was then purified by preparative reverse phase HPLC to provide the desired product as the diacetate salt. 1H NMR (DMSO-d6, 400 MHz) δ 7.89 (s, 1H), 7.39 (s, 1H), 6.82 (s, 1H), 6.73 (s, 2H), 6.20 (m, 1H), 5.65 (br s, 2H), 3.78 (s, 3H), 3.30 (d, 2H), 2.56 (q, 4H), 1.88 (s, 6H), 1.01 (t, 6H); MS m/e 383.4 (M+H)+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was then purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-eb6807a5ed60449b97990189d097d85e
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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