2,2-Dimethylbutyryl chloride → HCID 57937321, compound

HRID 1435459Notes

Reaction equation

HRID 1435459 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:19])[CH3:18])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[CH3:20][C:21]([CH3:27])([CH2:25][CH3:26])[C:22](Cl)=[O:23]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:17]([NH:16][C:4]1[CH:5]=[CH:6][C:7]([NH:8][CH2:9][CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[C:2]([NH:1][C:22](=[O:23])[C:21]([CH3:27])([CH3:20])[CH2:25][CH3:26])[CH:3]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 799582,2-Dimethylbutyryl chlorideHCID 57937312N-{3-Amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide

Product 1

HCID 57937321HCID 57937321, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Following the same procedure in Example 1, Step E, using N-{3-Amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide (10.5 g, 40 mmol), DMAP (2.4 g, 20 mmol) and 2,2-dimethylbutyryl chloride (5.9 g, 44 mmol) in 350 mL of DCM. Yield: 14.2 g (98%); 1H NMR (400 MHz, CHLOROFORM-D) δ 0.94 (t, J=7.52 Hz, 3 H), 1.29 (s, 6 H), 1.32-1.46 (m, 2 H), 1.66 (q, J=7.42 Hz, 2 H), 1.68-1.75 (m, 2 H), 1.78-1.90 (m, 1 H), 2.13 (s, 3 H), 2.97 (d, J=7.03 Hz, 2 H), 3.34-3.45 (m, 2 H), 3.77-3.86 (m, 1 H), 3.94-4.06 (m, 2 H), 6.75 (d, J=8.79 Hz, 1 H), 7.05 (s, 1 H), 7.21 (dd, J=8.59, 2.54 Hz, 1 H), 7.49 (s, 1 H), 7.55 (d, J=2.34 Hz, 1 H); MS (ESI) (M+H)+=362.06.

Sources & evidence

ORD record
ord-590f1e10bb494d43b59db3dbb93f41fb
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…