Acetyl chloride → HCID 11951617, compound

HRID 30156Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[S:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)=[O:8].[C:23](Cl)(=[O:25])[CH3:24]>O1CCCC1.C(Cl)(Cl)Cl.N1C=CC=CC=1.C(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]2)[S:5][C:6]=1[C:7](=[O:8])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1

Participants

Conditions

Temperature: -10 °C

Procedure

[4-Amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluorophenyl)methanone (0.10 g, 0.31 mmol) (Example 6) was dissolved in a mixture of tetrahydrofuran (20 mL), chloroform (6 mL), and pyridine and cooled to −10° C. This was treated with acetyl chloride (0.032 g, 43 mmol) and stirred for 0.5 hr. at room temperature. This was diluted with cold methylene chloride (100 mL) and washed with 10% Na2CO3(aq) (2×). After drying (Na2SO4) and solvent removal, the residue was precipitated from a mixture of tetrahydrofuran and hexane to give 35 mg (30% yield) of 1-[4-[4-amino-5-(3-fluorobenzoyl)thiazol-2-ylamino]piperidin-1-yl]ethanone. 1H NMR (DMSO−d6, 300 MHz) δ1.28 (m, 1H, CH), 1.41 (m, 1H, CH) 1.92 (m, 2H, CH2), 2.75 (t, 1H, NCH), 3.14 (t, H, NCH), 3.32 (s, 3H, COCH3), 3.6-4.0 (broad, 1H, CH), 3.77 (d, 1H, NCH), 4.22 (d, 1H, NCH), 7.31 (t, 1H, Aromatic), 7.38 (d, 1H, Aromatic), 7.48 (t, 1H, Aromatic), 7.51 (q, 1H, Aromatic), 8.01 (brd, 1H, NH), 8.48 (brd, 1H, NH), 8.72 (brd, 1H, NH). HRMS: (M+H)+: observed: 363.1288; calcd for 363.1286.

Workup

customat room temperature
washwashed with 10% Na2CO3(aq) (2×)
customAfter drying
custom(Na2SO4) and solvent removal
customthe residue was precipitated from a mixture of tetrahydrofuran and hexane

Sources & evidence

ORD record: ord-c34bfc567e6a4f608ece1dead8b8ccfe
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423053B2

Reaction notes

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