Acetone → Acetoacetic Acid

HRID 1270883Notes

Reaction equation

HRID 1270883 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-9d4ec92e7a57440e88778bd3eb54443e
Source dataset
uspto-grants-2007_04
Patent number
US07202363B2

Reaction notes

Loading…