Isopropyl chloroformate → HCID 24994034, compound

HRID 423509Notes

Reaction equation

HRID 423509 reaction equation
Cl.Cl.[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5].C(N(C(C)C)CC)(C)C.Cl[C:37]([O:39][CH:40]([CH3:42])[CH3:41])=[O:38]>>[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([C:37]([O:39][CH:40]([CH3:42])[CH3:41])=[O:38])[CH2:23][CH2:22]3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:5])=[O:6]

Participants

4

Reactant 3

HCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 66673101HCID 66673101, compound

Product 1

HCID 24994034HCID 24994034, compoundYield 98%

Procedure

The title compound (151 mg, 98%) was prepared as a white solid 5-[4-(methylsulfonyl)phenyl]-2-[(4-piperidinylmethyl)oxy]pyridine dihydrochloride (0.15 g, 0.36 mmol), diisopropylethylamine (0.26 mL, 1.43 mmol), and isopropyl chloroformate (1.0M in toluene, 0.40 mL, 0.40 mmol) in a manner similar to Example 66, Step 2. 1H NMR (400 MHz, CD3OD): δ 8.46 (d, 1H, J=2.4 Hz), 8.10-8.00 (m, 3H), 7.86 (d, 2H, J=8.3 Hz), 6.92 (d, 1H, J=8.5 Hz), 4.90-4.80 (m, 1H), 4.21 (d, 2H, J=6.3 Hz), 4.20-4.10 (m, 2H), 3.14 (s, 3H), 2.90-2.75 (m, 2H), 2.10-2.00 (m, 1H), 1.90-1.80 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 433 (M+H).

Sources & evidence

ORD record
ord-5c70cdd4ca60405eaccfc1ec32346e46
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

Loading…